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

HRID 1366433Notes

Reaction equation

HRID 1366433 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][NH:11][C:12](=[O:32])[C@H:13]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:14][N:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[O:17])[C:3]=1[F:33].[CH2:34]([N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)[CH3:35].C(N(C(C)C)CC)(C)C>CS(C)=O>[CH:27]1([CH2:26][C@@H:13]([C:12]([NH:11][NH:10][C:4]2[C:3]([F:33])=[C:2]([N:39]3[CH2:40][CH2:41][N:36]([CH2:34][CH3:35])[CH2:37][CH2:38]3)[N:7]=[C:6]([O:8][CH3:9])[N:5]=2)=[O:32])[CH2:14][N:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=[O:17])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 791961-EthylpiperazineHCID 81531DiisopropylethylamineHCID 86636937[(2R)-3-{2-[6-Chloro-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

Product 1

HCID 86636936((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamideYield 83.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

[(2R)-3-{2-[6-Chloro-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.150 g, 0.31 mmol), commercially available 1-ethylpiperazine (0.080 mL, 0.63 mmol) and diisopropylethylamine (0.054 mL, 0.31 mmol) were stirred in DMSO (2 mL) overnight at 65° C. The reaction mixture was then purified by RP-HPLC to provide ((2R)-2-(cyclopentylmethyl)-3-{2-[6-(4-ethyl-1-piperazinyl)-5-fluoro-2-(methyloxy)-4-pyrimidinyl]hydrazino}-3-oxopropyl)[(phenylmethyl)oxy]formamide as a red solid (0.145 g, 83%). LCMS: (M+H)+=558.3.

Workup

  1. customThe reaction mixture was then purified by RP-HPLC

Sources & evidence

ORD record
ord-844d0db6a42442889484414b0362101d
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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