HCID 117926009, compound → HCID 71768809, compound

HRID 1746915Notes

Reaction equation

HRID 1746915 reaction equation
[NH2:1][C:2](=[O:37])[CH:3]([OH:36])[CH:4]([NH:12][C:13]([C:15]1[C:16]([N:21]2[CH:25]=[C:24]3[CH2:26][N:27]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][C:23]3=[N:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.C(#N)C>[NH2:1][C:2](=[O:37])[C:3](=[O:36])[CH:4]([NH:12][C:13]([C:15]1[C:16]([N:21]2[CH:25]=[C:24]3[CH2:26][N:27]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:28][C:23]3=[N:22]2)=[N:17][CH:18]=[CH:19][CH:20]=1)=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 117926009HCID 117926009, compound

Product 1

HCID 71768809HCID 71768809, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

Oxidation of tert-butyl 2-(3-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-ylcarbamoyl)pyridin-2-yl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate (88 mg, 0.174 mmol) as described in example 1.4 and purification by chromatography over Chromabond RP-C18 (eluent: water/acetonitrile) gave 55 mg of an amorphous solid; ESI-MS [M+H]+: 505.2. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.83 (m, 1H), 8.52 (m, 1H), 8.15 (m, 1H), 8.06 (m, 1H), 7.84 (m, 1H), 7.72 (m, 1H), 7.44 (m, 1H), 7.23 (m, 4H), 7.17 (m, 1H), 5.26 (m, 1H), 4.35 (m, 2H), 4.18 (m, 1H), 4.0 (m, 1H), 3.09 (m, 1H), 2.73 (m, 1H), 1.49 (s, 9H).

Sources & evidence

ORD record
ord-5f6784c378af4e7f947d987febf5d1bb
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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