Imatinib → 4-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

HRID 2243397Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH:21][C:22]([C:24]2[CH:25]=[CH:26][C:27]([CH2:30]N3CCN(C)CC3)=[CH:28][CH:29]=2)=[O:23])=[CH:6][C:7]=1[NH:8][C:9]1[N:10]=[CH:11][CH:12]=[C:13]([C:15]2[CH:16]=[CH:17][CH:18]=[N:19][CH:20]=2)[N:14]=1.[Cl:38]CC1C=CC(C(Cl)=O)=CC=1>>[Cl:38][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]([NH:21][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[C:7]([NH:8][C:9]3[N:14]=[C:13]([C:15]4[CH:20]=[N:19][CH:18]=[CH:17][CH:16]=4)[CH:12]=[CH:11][N:10]=3)[CH:6]=2)=[O:23])=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 5291Imatinib

HCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 101810754-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

Procedure

Scheme 3 illustrates a third synthetic pathway for preparation of imatinib base, referred to herein as “Method C.” This method is described in WO 2004/108699 and in J. Med. Chem. 2005, 48(1), 249-255, and comprises the condensation of 4-methyl-N-3-(4-pyridin-3-yl-pyrimidin-2-yl)benzene-1,3-diamine with 4-chloromethylbenzoyl chloride to yield 4-chloromethyl-N-(4-methyl-3-((4-pyridin-3-yl)-pyrimidin-2-ylamino)-phenyl)-benzamide, followed by the reaction of 4-chloromethyl-N-(4-methyl-3-((4-pyridin-3-yl)-pyrimidin-2-ylamino)-phenyl)-benzamide with N-methylpiperazine.

Sources & evidence

ORD record: ord-d5e6232af98f427e85474f8c3df3a678
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674901B2

Reaction notes

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