1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide → 1-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carbonitrile

HRID 971138Notes

Reaction equation

HRID 971138 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:30])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([CH2:27][NH:28][CH3:29])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:31]([NH2:33])=O)=[N:10]2)=[CH:5][CH:4]=1>CN(C=O)C.S(Cl)(Cl)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]3[C:14](=[O:30])[N:15]([C:18]4[CH:23]=[CH:22][C:21]([C:24]5([CH2:27][NH:28][CH3:29])[CH2:25][CH2:26]5)=[CH:20][CH:19]=4)[CH2:16][CH2:17][C:12]=3[C:11]([C:31]#[N:33])=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 445813621-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carboxamide

Product 1

HCID 445813631-(4-Methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1h-pyrazolo[3,4-c]pyridine-3-carbonitrileYield 76.4%

Reagents, catalysts & solvents 2

HCID 24386Thionyl ChlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

The product of Example 67 (15 mg) was stirred in DMF (0.5 mL) at RT in a capped vial. Two drops of thionyl chloride was added. The reaction was completed in 10 min. The mixture was purified by RP-prep LC-MS (5–98% CH3CN/H2O in a 10-min run) to give pure 1-(4-methoxyphenyl)-6-(4-{1-[(methylamino)methyl]cyclopropyl}phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carbonitrile (11 mg, yield: 76.2%). LC/MS (ESI+) 428.4 (M+H)+, tR=4.49 min.

Workup

  1. customThe mixture was purified by RP-prep LC-MS (5–98% CH3CN/H2O in a 10-min run)

Sources & evidence

ORD record
ord-7e610fdf21e84e34ab9504f2fb4f01ef
Source dataset
uspto-grants-2007_12
Patent number
US07312214B2

Reaction notes

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