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molecular formula C27H28N4O5 B194352 ethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate CAS No. 503614-91-3

ethyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

Cat. No. B194352
M. Wt: 488.5 g/mol
InChI Key: PULNLYVCJSOXKS-UHFFFAOYSA-N
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Patent
US07153960B2

Procedure details

A solution of chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester (34, 470 mg, 1.3 mmol) in EtOAc (4 mL) was treated with 3-morpholin-4-yl-1-[4-(2-oxo-piperidin-1-yl)-phenyl]-5,6-dihydro-1H-pyridin-2-one (63, 334 mg, 1.3 mmol, 1.0 equiv) at 0–5° C. under N2, and the resulting reaction mixture was treated with triethylamine (TEA, 263 mg, 0.33 mL, 2.6 mmol, 2.0 equiv) at 0–5° C. under N2. The reaction mixture was then warmed up to room temperature for 30 min before being warmed up to reflux for an additional 6 h. When HPLC and TLC showed that the reaction was complete, the reaction mixture was cooled down to 5–10° C. before being treated dropwise with a 4.0 N aqueous HCl solution (1.7 mL, 6.5 mmol, 5.0 equiv) at 0–5° C. The resulting mixture was stirred at 5–20° C. for 4 h. The resulting slurry was then treated with water (10 mL) and EtOAc (10 mL) before the two layers were separated. The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic extracts were washed with saturated NaCl aqueous solution (5 mL), dried over MgSO4, and concentrated in vacuo. The residue was directly purified by flash column chromatography (SiO2, 15–40% EtOAc/hexane gradient elution) to afford the desired 1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (65, 423 mg, 635 mg theoretical, 67% for two steps) as pale-yellow solids, which solidified upon standing in vacuo at room temperature. For 65, CIMS m/z 489 (M++H, C27H28N4O5).
Name
chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester
Quantity
470 mg
Type
reactant
Reaction Step One
Name
Quantity
4 mL
Type
solvent
Reaction Step One
Quantity
0.33 mL
Type
reactant
Reaction Step Two
Name
Quantity
1.7 mL
Type
reactant
Reaction Step Three
Name
Quantity
10 mL
Type
solvent
Reaction Step Four

Identifiers

REACTION_CXSMILES
[CH2:1]([O:3][C:4](=[O:17])[C:5](Cl)=[N:6][NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)[CH3:2].N1([C:24]2[C:25](=[O:43])[N:26]([C:30]3[CH:35]=[CH:34][C:33]([N:36]4[CH2:41][CH2:40][CH2:39][CH2:38][C:37]4=[O:42])=[CH:32][CH:31]=3)[CH2:27][CH2:28][CH:29]=2)CCOCC1.C(N(CC)CC)C.Cl>CCOC(C)=O.O>[CH2:1]([O:3][C:4]([C:5]1[C:39]2[CH2:40][CH2:41][N:36]([C:33]3[CH:32]=[CH:31][C:30]([N:26]4[CH2:27][CH2:28][CH2:29][CH2:24][C:25]4=[O:43])=[CH:35][CH:34]=3)[C:37](=[O:42])[C:38]=2[N:7]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:6]=1)=[O:17])[CH3:2]

Inputs

Step One
Name
chloro[(4-methoxyphenyl)hydrazono]acetic acid ethyl ester
Quantity
470 mg
Type
reactant
Smiles
C(C)OC(C(=NNC1=CC=C(C=C1)OC)Cl)=O
Name
Quantity
334 mg
Type
reactant
Smiles
N1(CCOCC1)C=1C(N(CCC1)C1=CC=C(C=C1)N1C(CCCC1)=O)=O
Name
Quantity
4 mL
Type
solvent
Smiles
CCOC(=O)C
Step Two
Name
Quantity
0.33 mL
Type
reactant
Smiles
C(C)N(CC)CC
Step Three
Name
Quantity
1.7 mL
Type
reactant
Smiles
Cl
Step Four
Name
Quantity
10 mL
Type
solvent
Smiles
CCOC(=O)C
Name
Quantity
10 mL
Type
solvent
Smiles
O

Conditions

Temperature
Control Type
AMBIENT
Stirring
Type
CUSTOM
Details
The resulting mixture was stirred at 5–20° C. for 4 h
Rate
UNSPECIFIED
RPM
0
Other
Conditions are dynamic
1
Details
See reaction.notes.procedure_details.

Workups

CUSTOM
Type
CUSTOM
Details
the resulting reaction mixture
TEMPERATURE
Type
TEMPERATURE
Details
before being warmed up
TEMPERATURE
Type
TEMPERATURE
Details
to reflux for an additional 6 h
Duration
6 h
TEMPERATURE
Type
TEMPERATURE
Details
the reaction mixture was cooled down to 5–10° C.
CUSTOM
Type
CUSTOM
Details
were separated
EXTRACTION
Type
EXTRACTION
Details
The aqueous layer was extracted with EtOAc (2×10 mL)
WASH
Type
WASH
Details
The combined organic extracts were washed with saturated NaCl aqueous solution (5 mL)
DRY_WITH_MATERIAL
Type
DRY_WITH_MATERIAL
Details
dried over MgSO4
CONCENTRATION
Type
CONCENTRATION
Details
concentrated in vacuo
CUSTOM
Type
CUSTOM
Details
The residue was directly purified by flash column chromatography (SiO2, 15–40% EtOAc/hexane gradient elution)

Outcomes

Product
Details
Reaction Time
4 h
Name
Type
product
Smiles
C(C)OC(=O)C1=NN(C=2C(N(CCC21)C2=CC=C(C=C2)N2C(CCCC2)=O)=O)C2=CC=C(C=C2)OC
Measurements
Type Value Analysis
AMOUNT: MASS 423 mg
YIELD: PERCENTYIELD 67%
YIELD: CALCULATEDPERCENTYIELD 66.6%

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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