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

HRID 706841Notes

Reaction equation

HRID 706841 reaction equation
[CH:1]1([NH:5][C:6]2[N:7]=[N:8][C:9]([C:12]#[CH:13])=[CH:10][CH:11]=2)[CH2:4][CH2:3][CH2:2]1.[Cl:14][C:15]1[CH:39]=[CH:38][C:18]([C:19]([NH:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([N:32]3[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]3)[CH:23]=2)=[O:20])=[CH:17][C:16]=1I>>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([NH:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:29])[F:30])[CH:25]=[C:24]([N:32]3[CH:36]=[C:35]([CH3:37])[N:34]=[CH:33]3)[CH:23]=2)=[O:20])=[CH:38][C:39]=1[C:13]#[C:12][C:9]1[N:8]=[N:7][C:6]([NH:5][CH:1]2[CH2:4][CH2:3][CH2:2]2)=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 86709554N-Cyclobutyl-6-ethynylpyridazin-3-amineHCID 867095644-chloro-3-iodo-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 729502544-Chloro-3-(2-(6-(cyclobutylamino)pyridazin-3-yl)ethynyl)-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

Procedure

The title compound was synthesized from N-cyclobutyl-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 product was obtained as a pale yellow solid. Mp: 225-227° C.; 1H NMR (300 MHz, DMSO-d6) δ: 10.82 (1 H, s), 8.35 (1 H, d, J=2.1 Hz), 8.27 (1 H, s), 8.13 (1 H, s), 7.99-8.03 (1 H, dd, J=2.1 and 8.1 Hz), 7.81-7.84 (1 H, d, J=8.7 Hz), 7.76 (1 H, s), 7.66-7.68 (2 H, m), 7.46-7.49 (1 H, d, J=9.0 Hz), 6.76-6.80 (1 H, d, J=9.3 Hz), 4.40 (1 H, m), 2.32-2.34 (2 H, m), 2.17 (3 H, brs), 1.87-1.97 (2 H, m), 1.71-1.76 (2 H, m). HRMS (ESI-TOF+): m/z [M+2H]+2 calcd for C28H24ClF3N6O: 276.0821. found: 276.0819.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-bb1573aa8cbd4bc4a47c1d806bbde6ca
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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