N-cyclopropyl-6-ethynylpyridazin-3-amine → 6-(2-(2-Chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-cyclopropylpyridazin-3-amine

HRID 706811Notes

Reaction equation

HRID 706811 reaction equation
[CH:1]1([NH:4][C:5]2[N:6]=[N:7][C:8]([C:11]#[CH:12])=[CH:9][CH:10]=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[N:7]=[N:6][C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 86709556N-cyclopropyl-6-ethynylpyridazin-3-amineHCID 867095582-(4-chloro-3-iodophenyl)-6-((4-methylpiperazin-1-yl)methyl)-1H-benzoimidazole

Product 1

HCID 729495586-(2-(2-Chloro-5-(6-((4-methylpiperazin-1-yl)methyl)-1H-benzo[d]imidazol-2-yl)phenyl)ethynyl)-N-cyclopropylpyridazin-3-amine

Procedure

The title compound was synthesized from N-cyclopropyl-6-ethynylpyridazin-3-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 khaki solid. Mp: 130-131° C.; 1H NMR (300 MHz, CDCl3) δ: 8.11-8.13 (1 H, d, J=6.0 Hz), 7.86 (1 H, s), 7.64 (2 H, m), 7.42-7.45 (1 H, d, J=9.0 Hz), 7.39-7.42 (1 H, d, J=9.0 Hz), 7.22 (1 H, s), 7.01-7.04 (1 H, d, J=9.0 Hz), 6.00 (1 H, s), 3.61 (2 H, s), 2.60 (1 H, m), 2.44 (8 H, brs), 2.27 (3 H, s), 0.87-0.89 (2 H, m), 0.65 (2 H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C28H29ClN7: 498.2167. found: 498.2150.

Sources & evidence

ORD record
ord-1dc30b460adf4f3981e04c31232a7492
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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