N-cyclopropyl-5-ethynylpyrimidin-2-amine → 5-(2-(2-Chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-cyclopropylpyrimidin-2-amine

HRID 535827Notes

Reaction equation

HRID 535827 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]=[CH:9][C:8]([C:11]#[CH:12])=[CH:7][N:6]=2)[CH2:3][CH2:2]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:24][C:23]3[CH:25]=[C:26]([CH2:29][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:27]=[CH:28][C:22]=3[N:21]=2)=[CH:16][C:15]=1I>>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[NH:24][C:23]3[CH:25]=[C:26]([CH2:29][N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:27]=[CH:28][C:22]=3[N:21]=2)=[CH:16][C:15]=1[C:12]#[C:11][C:8]1[CH:9]=[N:10][C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 71512031N-cyclopropyl-5-ethynylpyrimidin-2-amineHCID 867095582-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzoimidazole

Product 1

HCID 729497325-(2-(2-Chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-cyclopropylpyrimidin-2-amine

Procedure

The title compound was synthesized from N-cyclopropyl-5-ethynylpyrimidin-2-amine and 2-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazole in a manner similar to that described for in Example 1. The title compound was obtained as a brown solid. Mp: 160-162° C.; 1H NMR (300 MHz, CDCl3) δ: 8.43-8.45 (2H, d, J=6.0 Hz), 8.12-8.15 (1H, d, J=6.0 Hz), 7.58-7.60 (1H, d, J=6.0 Hz), 7.52 (1H, s), 7.45-7.47 (1H, d, J=6.0 Hz), 7.38-7.40 (1H, d, J=6.0 Hz), 7.15-7.17 (1H, d, J=6.0 Hz), 5.80 (1H, s), 3.60 (2H, s), 2.80 (8H, brs), 2.59 (3H, s), 1.35-1.39 (1H, m), 0.82-0.88 (2H, m), 0.58-0.60 (2H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C28H29ClN7: 498.2167. found: 498.2163.

Sources & evidence

ORD record
ord-9818af45782747e1a8de093f62b96b5a
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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