HCID 89851572, compound → HCID 71768846, compound

HRID 1746919Notes

Reaction equation

HRID 1746919 reaction equation
[NH2:1][C:2](=[O:38])[CH:3]([OH:37])[CH:4]([NH:12][C:13](=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH:35]=[C:23]2[N:24]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:25][CH2:26][CH2:27][C:22]2=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>ClCCl.CO>[NH2:1][C:2](=[O:38])[C:3](=[O:37])[CH:4]([NH:12][C:13](=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH:35]=[C:23]2[N:24]([CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:25][CH2:26][CH2:27][C:22]2=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 89851572HCID 89851572, compound

Product 1

HCID 71768846HCID 71768846, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Oxidation of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(4-benzyl-4,5,6,7-tetrahydro-2H-pyrazolo[4,3-b]pyridin-2-yl)nicotinamide (150 mg, 0.294 mmol) as described in example 2.4 and purification by chromatography over silica gel (eluent: dichloromethane/methanol) afforded the title compound as an amorpous solid; 11 mg, ESI-MS [M+H]+: 509.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.62 (m, 1H), 8.35 (m, 2H), 7.76 (m, 1H), 7.50 (m, 1H), 7.35-7.12 (m, 12H), 5.85 (s, 1H), 4.36 (m, 1H), 4.20 (s, 2H), 3.20 (m, 2H), 2.93 (m, 2H), 2.71 (m, 3H), 1.94 (m, 2H).

Sources & evidence

ORD record
ord-997fb83e4c184d8cb219fb97f2f35045
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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