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

HRID 706835Notes

Reaction equation

HRID 706835 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].[Cl:13][C:14]1[CH:38]=[CH:37][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([C:33]([F:36])([F:35])[F:34])[CH:22]=2)=[O:19])=[CH:16][C:15]=1I>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH:31]=[C:30]([CH3:32])[N:29]=[CH:28]3)=[C:23]([C:33]([F:35])([F:34])[F:36])[CH:22]=2)=[O:19])=[CH:37][C:38]=1[C:12]#[C:11][C:8]1[N:7]=[N:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 86709557N-isopropyl-6-ethynylpyridazin-3-amineHCID 867095634-chloro-3-iodo-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729500824-Chloro-3-(2-(6-(isopropylamino)pyridazin-3-yl)ethynyl)-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 4-chloro-3-iodo-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:133-135° C.; 1H NMR (300 MHz, CDCl3) δ: 10.46 (1 H, s), 8.40 (1 H, s), 8.28-8.31 (1 H, d, J=8.1 Hz), 8.04 (1 H, s), 7.82-7.84 (1 H, d, J=8.1 Hz), 7.53 (1 H, s), 7.41-7.43 (1 H, d, J=8.4 Hz), 7.34-7.36 (2 H, m), 6.81 (1 H, s), 6.66-6.69 (1 H, d, J=9.3 Hz), 5.13-5.15 (1 H, d, J=6.3 Hz), 4.08 (1 H, m), 2.29 (3 H, s), 1.30-1.32 (6 H, d, J=6.0 Hz). HRMS (ESI-TOF+): m/z [M+H]+ calcd for C27H23ClF3N6O: 539.1568. found: 539.1592.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-f170fb5242b1424095b9ca754d2fad10
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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