N-Cyclobutyl-6-ethynylpyridazin-3-amine → HCID 72950081, compound

HRID 706834Notes

Reaction equation

HRID 706834 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]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([C:34]([F:37])([F:36])[F:35])[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]=[CH:26][C:25]([N:28]3[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]3)=[C:24]([C:34]([F:36])([F:35])[F:37])[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 867095634-chloro-3-iodo-N-(4-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl)benzamide

Product 1

HCID 72950081HCID 72950081, compound

Procedure

The title compound was synthesized from N-cyclobutyl-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:153-155° C.; 1H NMR (300 MHz, CDCl3) δ: 10.34 (1 H, s), 8.36 (1 H, s), 8.24-8.27 (1 H, d, J=8.1 Hz), 8.03 (1 H, s), 7.82-7.85 (1 H, d, J=8.1 Hz), 7.48 (1 H, s), 7.41-7.44 (1 H, d, J=8.7 Hz), 7.34-7.37 (2 H, t, J=9.3 and 8.7 Hz), 6.80 (1 H, s), 6.61-6.64 (1 H, d, J=9.6 Hz), 5.57-5.59 (1 H, d, J=6.0 Hz), 4.22-4.29 (1 H, m), 2.45-2.48 (2 H, m), 2.28 (3 H, s), 1.76-2.01 (4 H, m). HRMS (ESI-TOF+): m/z [M+2H]+2 calcd for C28H24ClF3N6O: 276.0821. found: 276.0817.

Workup

  1. customThe product was obtained as a pale yellow solid

Sources & evidence

ORD record
ord-c8d10756d8064fd2bdbba588c5867336
Source dataset
uspto-grants-2015_11
Patent number
US09174996B2

Reaction notes

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