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

HRID 1441318Notes

Reaction equation

HRID 1441318 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:32]=[CH:31][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([Cl:30])=[CH:17][N:16]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=O)C>CCOCC>[N:7]1([C:10]2[CH:11]=[CH:12][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[C:18]([Cl:30])=[CH:17][N:16]=3)=[CH:31][CH:32]=2)[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

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

Product 1

HCID 686895762-[4-(piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The title compound was prepared from 2-[4-(4-acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)-5-chloropyrimidine (Example 33; 800 mg) by the method of Example 20. Except that after purification by chromatography on neutral alumina, activity II eluting with MeOH:DCM (3:97) the title compound was isolated as a yellow gum. Trituration with ether gave a foam (50 mg 7%). NMR: 1.34 (d, 6H), 2.45 (s, 3H), 2.82 (m, 4H), 2.96 (m, 4H), 4.82 (septuplet, 1H), 6.85 (d, 2H), 7.41 (s, 1H), 7.42 (d, 2H), 8.49 (s, 1H), 9.43 (s, 1H); m/z 412.

Workup

  1. customExcept that after purification by chromatography on neutral alumina, activity II
  2. washeluting with MeOH:DCM (3:97) the title compound
  3. customwas isolated as a yellow gum

Sources & evidence

ORD record
ord-54d8574b030f4b939a3537f8f92568ab
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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