HCID 89853201, compound → HCID 71768672, compound

HRID 1746911Notes

Reaction equation

HRID 1746911 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[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[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[CH2:35][CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27]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 89853201HCID 89853201, compound

Product 1

HCID 71768672HCID 71768672, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxidation of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(3-((3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1H-pyrazol-1-yl)nicotinamide (200 mg, 0.392 mmol) as described in example 1.4, recrystallization of the crude product from CH2Cl2/MTB gave the title compound as white amorphous solid; 52 mg, ESI-MS [M+H]+: 509.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.98 (m, 1H), 8.59 (m, 1H), 8.42 (m, 1H), 8.07 (m, 1H), 7.83 (m, 1H), 7.74 (m, 1H), 7.44 (m, 1H), 7.29-7.15 (m, 5H), 7.10-7.00 (m, 4H), 6.43 (m, 1H), 5.43 (m, 1H), 3.48 (m, 4H), 3.17 and 2.91 (each dd, 1H), 2.91 (m, 2H), 2.61 (m, 2H).

Sources & evidence

ORD record
ord-a5cd80d7cf3147e69d9da1a6f237e5e8
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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