Ethyl Acetate → HCID 71768707, compound

HRID 1746913Notes

Reaction equation

HRID 1746913 reaction equation
[NH2:1][C:2](=[O:35])[CH:3]([OH:34])[CH:4]([NH:12][C:13](=[O:33])[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][NH:26]C2C=CC=CC=2)=[N:21]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O[C:39](=O)[CH3:40])C>>[NH2:1][C:2](=[O:35])[C:3](=[O:34])[CH:4]([NH:12][C:13](=[O:33])[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[CH2:8][CH2:7][CH:6]([C:39]3[CH:40]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:11]2)=[N:21]1)[CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 89855572HCID 89855572, compound

Product 1

HCID 71768707HCID 71768707, compound

Procedure

Oxidation of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(3-((phenylamino)methyl)-1H-pyrazol-1-yl)nicotinamide (120 mg, 0.255 mmol) as described in example 1.4, subsequent crystallization of the crude product from 2-propanole and then from ethylacetate afforded the title compound as white amorphous solid; 80 mg, ESI-MS [M+H]+: 523.3. 1H-NMR (400 MHz, DMSO), δ[ppm]: 8.93 (m, 1H), 8.50 (m, 1H), 8.32 (m, 1H), 8.06 (m, 1H), 7.82 (m, 1H), 7.71 (m, 1H), 7.42-7.25 (m, 10H), 6.42 (m, 1H), 5.38 (m, 1H), 3.49 (m, 2H), 3.25 (m, 1H), 3.17 (dd, 1H), 2.88 (m, 2H), 2.63 (m, 2H), 2.39 (m, 1H), 2.21 (m, 1H), 1.72 (m, 1H).

Sources & evidence

ORD record
ord-4f2e50f67b33481fa5718b01716031fb
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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