2-Chloro-4-fluorobenzoyl chloride → 2-Chloro-N-(6-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-yl)-4-fluoro-benzamide di-hydrochloride salt
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH3:12][N:13]([CH3:27])[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[N:25]=[C:24]([NH2:26])[CH:23]=[CH:22][CH:21]=2)=[CH:16][CH2:15]1>>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:26][C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([C:17]2[CH2:18][CH2:19][CH:14]([N:13]([CH3:27])[CH3:12])[CH2:15][CH:16]=2)[N:25]=1)=[O:5]Participants
3
Procedure
Using a method similar to example 1, using 2-chloro-4-fluoro-benzoyl chloride (133 mg, 0.69 mmol) and 6-(4-dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine, isomer 2 (preparation 11, 100 mg, 0.46 mmol) provides the free amine of the title compound as an oil (110 mg, 64%): MS (ES): m/z=374.2 (M+H)+; 1H NMR (CD3OD): δ 8.36 (t, 1H), 7.73 (m, 3H), 7.47 (d, 1H), 7.32 (t, 1H), 6.86 (m, 1H), 3.62 (m, 1H), 2.97 (s, 6H), 2.74 (m, 4H), 2.47 (m, 1H), 1.99 (m, 1H). Using a salt formation method similar to that in example 1 gives the dihydrochloride salt.
Sources & evidence
- ORD record
- ord-839567d7c52541c48fb4f755c8dc76ba
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312236B2
Reaction notes
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