2-Piperazinylpyrimidine dihydrochloride → 2-(3,4-Difluoro-phenylamino)-N-[2-methyl-5-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-phenyl]-acetamide

HRID 1267931Notes

Reaction equation

HRID 1267931 reaction equation
C(OC(=O)[N:7]([C:21]1[CH:26]=[CH:25][C:24]([F:27])=[C:23]([F:28])[CH:22]=1)[CH2:8][C:9](=[O:20])[NH:10][C:11]1[CH:16]=[C:15]([CH2:17]O)[CH:14]=[CH:13][C:12]=1[CH3:19])(C)(C)C.Cl.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[N:34][C:33]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CS(C)=O>[F:28][C:23]1[CH:22]=[C:21]([NH:7][CH2:8][C:9]([NH:10][C:11]2[CH:16]=[C:15]([CH2:17][N:41]3[CH2:42][CH2:43][N:38]([C:33]4[N:32]=[CH:37][CH:36]=[CH:35][N:34]=4)[CH2:39][CH2:40]3)[CH:14]=[CH:13][C:12]=2[CH3:19])=[O:20])[CH:26]=[CH:25][C:24]=1[F:27]

Participants

4

Reactant 2

HCID 116802722-Piperazinylpyrimidine dihydrochlorideHCID 54088725(3,4-Difluoro-phenyl)-[(5-hydroxymethyl-2-methyl-phenylcarbamoyl)-methyl]-carbamic acid tert-butyl ester

Product 1

HCID 98684852-(3,4-Difluoro-phenylamino)-N-[2-methyl-5-(4-pyrimidin-2-yl-piperazin-1-ylmethyl)-phenyl]-acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared according to the procedure of Example 11c) using (3,4-difluoro-phenyl)-[(5-hydroxymethyl-2-methyl-phenylcarbamoyl)-methyl]-carbamic acid tert-butyl ester and 1-(2-pyrimidyl)piperazine dihydrochloride to give the title compound as a 10 mM solution in dimethyl sulfoxide. An aliquot (30 mL) of this solution was diluted with dimethyl sulfoxide/water (220 mL of a 1:1 mixture) was analysed by HPLC on a 20 mm×3.9 mm Waters Symmetry C8 column, eluting with 30%-95% acetonitrile/ammonium acetate.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-a473179035804d05bad4da8c26154966
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

Loading…