3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide → 3-(2-(6-(Cyclopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

HRID 535837Notes

Reaction equation

HRID 535837 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.I[C:14]1[CH:15]=[C:16]([CH:38]=[CH:39][C:40]=1[CH3:41])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][N:27]2[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]2)=[C:22]([C:34]([F:37])([F:36])[F:35])[CH:21]=1)=[O:18]>>[CH:1]1([NH:4][C:5]2[N:6]=[N:7][C:8]([C:11]#[C:12][C:39]3[CH:38]=[C:16]([CH:15]=[CH:14][C:40]=3[CH3:41])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH2:26][N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)=[C:22]([C:34]([F:37])([F:36])[F:35])[CH:21]=3)=[O:18])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 468389103-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamideHCID 86709556N-cyclopropyl-6-ethynylpyridazin-3-amine

Product 1

HCID 729497343-(2-(6-(Cyclopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from N-cyclopropyl-6-ethynylpyridazin-3-amine and 3-iodo-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide (as prepared above) in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp: 68-69° C.; 1H NMR (300 MHz, CDCl3) δ: 8.84 (1H, s), 7.99-8.01 (2H, d, J=6.0 Hz), 7.95-7.98 (1H, d, J=9.0 Hz), 7.82-7.85 (1H, d, J=9.0 Hz), 7.71-7.73 (1H, d, J=6.0 Hz), 7.40-7.43 (1H, d, J=9.0 Hz), 7.29-7.32 (1H, d, J=9.0 Hz), 6.99-7.02 (1H, d, J=9.0 Hz), 5.85 (1H, s), 3.63 (2H, s), 2.53 (8H, brs), 2.34 (3H, s), 2.03 (3H, s), 1.43 (1H, m), 0.86-0.88 (2H, m), 0.61-0.63 (2H, m). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C30H32F3N6O: 549.2584. found: 549.2568.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-81fb5b3ed6d24553b0d58e43fd9d5039
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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