2,4,6-Trifluorobenzoyl chloride → N-(6-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-yl)-2,4,6-trifluoro-benzamide dihydrochloride salt

HRID 970758Notes

Reaction equation

HRID 970758 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([F:12])[C:3]=1[C:4]([Cl:6])=[O:5].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[N:26]=[C:25]([NH2:27])[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH2:16]1>>[ClH:6].[ClH:6].[CH3:13][N:14]([CH3:28])[CH:15]1[CH2:20][CH2:19][C:18]([C:21]2[N:26]=[C:25]([NH:27][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:10][C:9]([F:11])=[CH:8][C:7]=3[F:12])[CH:24]=[CH:23][CH:22]=2)=[CH:17][CH2:16]1

Participants

3

Reactant 2

HCID 1448952,4,6-Trifluorobenzoyl chlorideHCID 588523656-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine

Product 1

HCID 69351067N-(6-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-yl)-2,4,6-trifluoro-benzamide dihydrochloride saltYield 46%

Procedure

Using a method similar to example 1, using 2,4,6-trifluoro-benzoyl chloride (134 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 (80 mg, 46%): MS (ES): m/z=376.2 (M+H)+; 1H NMR (CD3OD): δ 8.25 (t, 1H), 7.67 (d, 1H), 7.74 (d, 1H), 7.12 (t, 2H), 6.81 (m, 1H), 3.62 (m, 1H), 2.96 (s, 6H), 2.73 (m, 4H), 2.45 (m, 1H), 1.95 (m, 1H). Using a salt formation method similar to that in example 1 gives the dihydrochloride salt.

Sources & evidence

ORD record
ord-6d48c821c7664d75a4e53c3a1dc82ebc
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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