HCID 89855437, compound → HCID 71768673, compound

HRID 1746912Notes

Reaction equation

HRID 1746912 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:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]2)=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(Cl)Cl>[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:24]=[CH:23][C:22]([CH2:25][N:26]2[CH2:27][CH2:28][CH:29]([C:32]([CH3:34])([CH3:35])[CH3:33])[CH2:30][CH2:31]2)=[N:21]1)[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 89855437HCID 89855437, compound

Product 1

HCID 71768673HCID 71768673, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxidation of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(3-((4-tert-butylpiperidin-1-yl)methyl)-1H-pyrazol-1-yl)nicotinamide (200 mg, 0.386 mmol) as described in example 1.4, recrystallization of the crude product from CH2Cl2/MTB gave the title compound as white amorphous solid; 34 mg, ESI-MS [M+H]+: 517.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.94 (m, 1H), 8.52 (m, 1H), 8.30 (m, 1H), 8.05 (m, 1H), 7.82 (m, 1H), 7.74 (m, 1H), 7.43 (m, 5H), 6.37 (m, 1H), 5.36 (m, 1H), 3.27 (m, overlapping with water), 2.88 (m, 3H), 1.75 (m, 2H), 1.54 (m, 2 h), 1.15 (m, 2H), 0.82 (m, 11H).

Sources & evidence

ORD record
ord-4f3aad196fdc4193a4cee3dcc9191039
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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