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molecular formula C21H27N5 B1662892 Mavorixafor CAS No. 558447-26-0

Mavorixafor

Cat. No. B1662892
M. Wt: 349.5 g/mol
InChI Key: WVLHHLRVNDMIAR-IBGZPJMESA-N
Attention: For research use only. Not for human or veterinary use.
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Patent
US07354932B2

Procedure details

To a solution of N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (73 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (4 mL) and the resultant solution was stirred at room temperature overnight then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL) and water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase was basic (pH 14). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH) provided 37 mg of N-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Reaction Step One
Quantity
4 mL
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One
[Compound]
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]

Inputs

Step One
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Smiles
C[Si](CCOCN1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21)(C)C
Name
Quantity
4 mL
Type
reactant
Smiles
FC(C(=O)O)(F)F
Name
Quantity
2 mL
Type
solvent
Smiles
C(Cl)Cl
Step Two
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CONCENTRATION
Type
CONCENTRATION
Details
then concentrated under reduced pressure
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in CH2Cl2 (10 mL)
ADDITION
Type
ADDITION
Details
water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted with CH2Cl2 (3×10 mL)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic extracts were dried (Na2SO4)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated
CUSTOM
Type
CUSTOM
Details
Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH)

Outcomes

Product
Name
Type
product
Smiles
N1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21
Measurements
Type Value Analysis
AMOUNT: MASS 37 mg
YIELD: CALCULATEDPERCENTYIELD 66.2%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
Patent
US07354932B2

Procedure details

To a solution of N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine (73 mg, 0.16 mmol) in CH2Cl2 (2 mL) was added trifluoroacetic acid (4 mL) and the resultant solution was stirred at room temperature overnight then concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (10 mL) and water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase was basic (pH 14). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH) provided 37 mg of N-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine as a white foam.
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Reaction Step One
Quantity
4 mL
Type
reactant
Reaction Step One
Quantity
2 mL
Type
solvent
Reaction Step One
[Compound]
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Two

Identifiers

REACTION_CXSMILES
C[Si](C)(C)CCOC[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[CH2:16][N:17]([CH:23]1[C:32]2[N:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:26][CH2:25][CH2:24]1)[CH2:18][CH2:19][CH2:20][CH2:21][NH2:22]

Inputs

Step One
Name
N1-(1-(2-(trimethylsilyl)ethoxymethyl)-1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-diamine
Quantity
73 mg
Type
reactant
Smiles
C[Si](CCOCN1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21)(C)C
Name
Quantity
4 mL
Type
reactant
Smiles
FC(C(=O)O)(F)F
Name
Quantity
2 mL
Type
solvent
Smiles
C(Cl)Cl
Step Two
Name
resultant solution
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CONCENTRATION
Type
CONCENTRATION
Details
then concentrated under reduced pressure
DISSOLUTION
Type
DISSOLUTION
Details
The residue was dissolved in CH2Cl2 (10 mL)
ADDITION
Type
ADDITION
Details
water (5 mL) and treated with NaOH (10 M, ˜2 mL) until the aqueous phase
CUSTOM
Type
CUSTOM
Details
The phases were separated
EXTRACTION
Type
EXTRACTION
Details
the aqueous phase was extracted with CH2Cl2 (3×10 mL)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
The combined organic extracts were dried (Na2SO4)
CONCENTRATION
Type
CONCENTRATION
Details
concentrated
CUSTOM
Type
CUSTOM
Details
Purification of the crude material by radial chromatography on silica gel (1 mm plate, 15:1:1 CH2Cl2—CH3OH—NH4OH)

Outcomes

Product
Name
Type
product
Smiles
N1C(=NC2=C1C=CC=C2)CN(CCCCN)C2CCCC=1C=CC=NC21
Measurements
Type Value Analysis
AMOUNT: MASS 37 mg
YIELD: CALCULATEDPERCENTYIELD 66.2%

Source

Source
Open Reaction Database (ORD)
Description
The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.
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