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

HRID 970756Notes

Reaction equation

HRID 970756 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:6])=[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:6].[ClH:6].[CH3:12][N:13]([CH3:27])[CH:14]1[CH2:19][CH2:18][C:17]([C:20]2[N:25]=[C:24]([NH:26][C:4](=[O:5])[C:3]3[CH:7]=[CH:8][C:9]([F:11])=[CH:10][C:2]=3[F:1])[CH:23]=[CH:22][CH:21]=2)=[CH:16][CH2:15]1

Participants

3

Reactant 2

HCID 5880812,4-Difluorobenzoyl chlorideHCID 588523656-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine

Product 1

HCID 69350886N-(6-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-yl)-2,4-difluoro-benzamide dihydrochloride saltYield 35%

Procedure

Using a method similar to example 1, using 2,4-difluoro-benzoyl chloride (122 mg, 0.69 mmol) and 6-(4-dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine (preparation 11, 100 mg, 0.46 mmol) provides the free amine of the title compound as an oil (52 mg, 32%): MS(ES): m/z=358 (M+H)+; 1H NMR (CD3OD): δ 8.23 (t, 1H), 7.89 (m, 1H), 7.64 (m, 2H), 7.14 (m, 2H), 6.74 (m, 1H), 3.52 (m, 1H), 2.86 (s, 6H), 2.69 (m, 4H), 2.35 (m, 1H), 1.87 (m, 1H). Using a salt formation method similar to that in example 1 gives the dihydrochloride salt.

Sources & evidence

ORD record
ord-e4207ec733de4e91b9b77627aaa45394
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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