2-[4-(4-Mesylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine → 2-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine

HRID 1441317Notes

Reaction equation

HRID 1441317 reaction equation
Cl/[C:2](=C/N(C)C)/[C:3](C1N(C(C)C)C(C)=NC=1)=[O:4].S([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:50]=[CH:49][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]([CH3:46])[CH3:45])[C:42]([CH3:47])=[N:41][CH:40]=4)[C:36]([Cl:48])=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)(C)(=O)=O>COCCO>[C:3]([N:22]1[CH2:27][CH2:26][N:25]([C:28]2[CH:50]=[CH:49][C:31]([NH:32][C:33]3[N:38]=[C:37]([C:39]4[N:43]([CH:44]([CH3:45])[CH3:46])[C:42]([CH3:47])=[N:41][CH:40]=4)[C:36]([Cl:48])=[CH:35][N:34]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 686887152-[4-(4-Mesylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidineHCID 86613527(2E)-2-Chloro-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

Product 1

HCID 686865592-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

(2E)-2-Chloro-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (1.68 g from Method 3-assumed 5 mmol) and N-[4-(4-acetylpiperazin-1-yl)phenyl]guanidine bicarbonate salt (Method 2) (1.94 g 6 mmol) in 2-methoxyethanol (25 ml) were heated under nitrogen at 110° C. for 3.5 hours before evaporation under reduced pressure. The residue was purified by chromatography on silica gel with MeOH:DCM (3:97 to 5:95) to give the title compound, after trituration with ether, as a foam. NMR: 1.36 (d, 6H), 2.02 (s, 3H), 2.48 (s, 3H), 3.00 (b t, 2H), 3.08 (b t, 2H), 3.56 (b q, 4H), 4.80 (septuplet, 1H), 6.90 (d, 2H), 7.21 (s, 1H), 7.47 (d, 2H), 8.50 (s, 1H), 9.48 (s, 1H); m/z 454.

Workup

  1. customThe residue was purified by chromatography on silica gel with MeOH:DCM (3:97 to 5:95)

Sources & evidence

ORD record
ord-0add5a25ed3a4c3eb8137ff706cee50b
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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