N-cyclopropyl-6-ethynylpyridazin-3-amine → 3-(2-(6-(Cyclopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide

HRID 535846Notes

Reaction equation

HRID 535846 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:36]=[CH:37][C:38]=1[CH3:39])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]2)=[C:22]([C:32]([F:35])([F:34])[F:33])[CH:21]=1)=[O:18]>>[CH:1]1([NH:4][C:5]2[N:6]=[N:7][C:8]([C:11]#[C:12][C:37]3[CH:36]=[C:16]([CH:15]=[CH:14][C:38]=3[CH3:39])[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]4)=[C:22]([C:32]([F:33])([F:34])[F:35])[CH:21]=3)=[O:18])=[CH:9][CH:10]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 86709556N-cyclopropyl-6-ethynylpyridazin-3-amineHCID 867095623-iodo-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-3(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729499143-(2-(6-(Cyclopropylamino)pyridazin-3-yl)ethynyl)-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-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-methyl-1H-imidazol-1-yl)-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: 125-126° C.; 1H NMR (300 MHz, CDCl3) δ: 9.94 (1H, s), 8.34 (1H, s), 8.20-8.23 (1H, d, J=8.7 Hz), 8.02 (1H, s), 7.86-7.89 (1H, d, J=8.1 Hz), 7.53 (1H, s), 7.39-7.42 (1H, d, J=9.0 Hz), 7.30-7.32 (2H, m), 7.02-7.05 (1H, d, J=9.2 Hz), 6.80 (1H, s), 6.02 (1H, s), 2.58 (1H, m), 2.48 (3H, s), 2.29 (3H, s), 0.87 (2H, m), 0.64 (2H, brs). HRMS (ESI-TOF+): m/z [M+2H]+2 calcd for C28H25F3N6O: 259.1015. found: 259.1023.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-4f180b23df474abfa947cf80767955fb
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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