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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 (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.169 g, 0.451 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.25 mL, 1.44 mmol) followed by 4-bromobutyronitrile (0.10 mL, 1.01 mmol). The resultant mixture was heated to 80° C. for 5 d then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL). 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 column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH) provided 108 mg (54%) of a yellow foam.
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Reaction Step One
Quantity
0.25 mL
Type
reactant
Reaction Step One
Name
Quantity
5 mL
Type
solvent
Reaction Step One
Quantity
0.1 mL
Type
reactant
Reaction Step Two
[Compound]
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Yield
54%

Identifiers

REACTION_CXSMILES
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]#[N:43]>CC#N>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]

Inputs

Step One
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Smiles
C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21
Name
Quantity
0.25 mL
Type
reactant
Smiles
C(C)(C)N(C(C)C)CC
Name
Quantity
5 mL
Type
solvent
Smiles
CC#N
Step Two
Name
Quantity
0.1 mL
Type
reactant
Smiles
BrCCCC#N
Step Three
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CONCENTRATION
Type
CONCENTRATION
Details
The mixture was concentrated
CUSTOM
Type
CUSTOM
Details
the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL)
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 column chromatography on silica gel (30:1:1 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 108 mg
YIELD: PERCENTYIELD 54%
YIELD: CALCULATEDPERCENTYIELD 68.5%

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 (1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine (0.169 g, 0.451 mmol) in CH3CN (5 mL) was added N,N-diisopropylethylamine (0.25 mL, 1.44 mmol) followed by 4-bromobutyronitrile (0.10 mL, 1.01 mmol). The resultant mixture was heated to 80° C. for 5 d then cooled to room temperature. The mixture was concentrated and the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL). 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 column chromatography on silica gel (30:1:1 CH2Cl2—CH3OH—NH4OH) provided 108 mg (54%) of a yellow foam.
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Reaction Step One
Quantity
0.25 mL
Type
reactant
Reaction Step One
Name
Quantity
5 mL
Type
solvent
Reaction Step One
Quantity
0.1 mL
Type
reactant
Reaction Step Two
[Compound]
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Reaction Step Three
Yield
54%

Identifiers

REACTION_CXSMILES
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][NH:18][CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.C(N(CC)C(C)C)(C)C.Br[CH2:39][CH2:40][CH2:41][C:42]#[N:43]>CC#N>[NH:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:8]=[C:9]1[CH2:17][N:18]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:39][CH2:40][CH2:41][CH2:42][NH2:43]

Inputs

Step One
Name
(1-tert-butoxycarbonyl-1H-Benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine
Quantity
0.169 g
Type
reactant
Smiles
C(C)(C)(C)OC(=O)N1C(=NC2=C1C=CC=C2)CNC2CCCC=1C=CC=NC21
Name
Quantity
0.25 mL
Type
reactant
Smiles
C(C)(C)N(C(C)C)CC
Name
Quantity
5 mL
Type
solvent
Smiles
CC#N
Step Two
Name
Quantity
0.1 mL
Type
reactant
Smiles
BrCCCC#N
Step Three
Name
resultant mixture
Quantity
0 (± 1) mol
Type
reactant
Smiles

Conditions

Temperature
Control Type
AMBIENT
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CONCENTRATION
Type
CONCENTRATION
Details
The mixture was concentrated
CUSTOM
Type
CUSTOM
Details
the residue was partitioned between CH2Cl2 (20 mL) and brine (10 mL)
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 column chromatography on silica gel (30:1:1 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 108 mg
YIELD: PERCENTYIELD 54%
YIELD: CALCULATEDPERCENTYIELD 68.5%

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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