(2S)-2-{[6-{2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]hydrazino}-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamide → (2S)-2-{[6-[2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)hydrazino]-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamide

HRID 1366438Notes

Reaction equation

HRID 1366438 reaction equation
[CH:1]1([CH2:6][C@H:7]([CH2:30][N:31]([CH:40]=[O:41])[O:32]CC2C=CC=CC=2)[C:8]([NH:10][NH:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([NH:20][C@@H:21]([CH2:27][CH3:28])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:13]=2[F:29])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([CH2:6][C@H:7]([CH2:30][N:31]([CH:40]=[O:41])[OH:32])[C:8]([NH:10][NH:11][C:12]2[N:17]=[C:16]([O:18][CH3:19])[N:15]=[C:14]([NH:20][C@@H:21]([CH2:27][CH3:28])[C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[C:13]=2[F:29])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86636938(2S)-2-{[6-{2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]hydrazino}-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamide

Product 1

HCID 58000532(2S)-2-{[6-[2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)hydrazino]-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamideYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S)-2-{[6-{2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]hydrazino}-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamide (0.036 g, 0.063 mmol), and Pd(C) (0.008 g) in MeOH (10 mL) was run under standard hydrogenation conditions as in General Procedure A, Part C, to provide (2S)-2-{[6-[2-((2R)-3-cyclopentyl-2-{[formyl(hydroxy)amino]methyl}propanoyl)hydrazino]-5-fluoro-2-(methyloxy)-4-pyrimidinyl]amino}-N,N-dimethylbutanamide as an orange solid (0.019 g, 63%). LCMS: (M+H)+=484.4.

Sources & evidence

ORD record
ord-c6eb86780e87417cbccea291416e9dcd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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