((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide → ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide

HRID 1366434Notes

Reaction equation

HRID 1366434 reaction equation
[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:36][CH2:35][N:34]([CH2:37][CH3:38])[CH2:33][CH2:32]3)[N:27]=[C:26]([O:39][CH3:40])[N:25]=2)=[O:21])[CH2:8][N:9]([O:12]CC2C=CC=CC=2)[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO>[CH:1]1([CH2:6][C@@H:7]([C:20]([NH:22][NH:23][C:24]2[C:29]([F:30])=[C:28]([N:31]3[CH2:32][CH2:33][N:34]([CH2:37][CH3:38])[CH2:35][CH2:36]3)[N:27]=[C:26]([O:39][CH3:40])[N:25]=2)=[O:21])[CH2:8][N:9]([OH:12])[CH:10]=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 86636936((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide

Product 1

HCID 58000761((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamideYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide (0.145 g, 0.26 mmol), and Pd(C) (0.030 g) in MeOH (10 mL) was run under standard hydrogenation conditions as in General Procedure A, Part C, to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)hydroxyformamide as a red solid (0.119 g, 98%). LCMS: (M+H)+=468.4.

Sources & evidence

ORD record
ord-35f55b616b5046a9a34725f0444a892b
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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