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

HRID 535847Notes

Reaction equation

HRID 535847 reaction equation
[CH:1]([NH:4][C:5]1[N:6]=[N:7][C:8]([C:11]#[CH:12])=[CH:9][CH:10]=1)([CH3:3])[CH3:2].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]([NH:4][C:5]1[N:6]=[N:7][C:8]([C:11]#[C:12][C:37]2[CH:36]=[C:16]([CH:15]=[CH:14][C:38]=2[CH3:39])[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:22]([C:32]([F:33])([F:34])[F:35])[CH:21]=2)=[O:18])=[CH:9][CH:10]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 86709557N-isopropyl-6-ethynylpyridazin-3-amineHCID 867095623-iodo-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-3(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729500793-(2-(6-(Isopropylamino)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-isopropyl-6-ethynylpyridazin-3-amine and 3-iodo-4-methyl-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide in a manner similar to that described for in Example 1. The product was obtained as a pale yellow solid. Mp: 141-143° C.; 1H NMR (300 MHz, CDCl3) δ: 9.82 (1H, s), 8.34 (1H, s), 8.20-8.23 (1H, d, J=7.8 Hz), 7.96 (1H, s), 7.84-7.86 (1H, d, J=8.1 Hz), 7.54 (1H, s), 7.29-7.31 (3H, m), 6.81 (1H, s), 6.63-6.66 (1H, d, J=8.4 Hz), 5.11 (1H, brs), 4.08 (1H, m), 2.46 (3H, s), 2.29 (3H, s), 1.28-1.31 (6H, d, J=6.3 Hz). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C28H26F3N6O: 519.2115. found: 519.2116.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-03f319643ba64f89a1c47d983677b17b
Source dataset
uspto-grants-2014_10
Patent number
US08859553B2

Reaction notes

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