N-cyclopropyl-6-ethynylpyridazin-3-amine → 4-Chloro-3-(2-(6-(cyclopropylamino)pyridazin-3-yl)ethynyl)-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 706840Notes

Reaction equation

HRID 706840 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:38]=[CH:37][C:17]([C:18]([NH:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)[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]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:24]=[C:23]([N:31]3[CH:35]=[C:34]([CH3:36])[N:33]=[CH:32]3)[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]2[CH2:3][CH2:2]2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 86709556N-cyclopropyl-6-ethynylpyridazin-3-amineHCID 867095644-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide2×

Product 1

HCID 729502534-Chloro-3-(2-(6-(cyclopropylamino)pyridazin-3-yl)ethynyl)-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from N-cyclopropyl-6-ethynylpyridazin-3-amine and 4-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl) benzamide in a manner similar to that described for in Example 1. The intermediate compound 4-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide was made as for Example 24 (Step 1 to 2) with the spectra below: 1H NMR (300 MHz, DMSO-d6) δ: 10.78 (1 H, s), 8.55 (1 H, d, J=2.1 Hz), 8.26 (1 H, s), 8.22 (1 H, s), 8.11 (1 H, s), 7.99-8.03 (1 H, dd, J=2.1 and 8.1 Hz), 7.76-7.80 (2 H, m), 7.49 (1 H, s), 2.19 (3 H, s). LCMS: m/z [M+H]+ 505.9663.

Sources & evidence

ORD record
ord-f7b5bc55afb7457280ee6fe536202779
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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