2,4-Difluorobenzoyl chloride → HCID 69351527, compound

HRID 970753Notes

Reaction equation

HRID 970753 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].[F: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

Reactant 2

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

Product 1

HCID 69351527HCID 69351527, compoundYield 94%

Procedure

Using a method similar to example 24, using 2,4-difluoro-benzoyl chloride (141 mg, 0.80 mmol) and 6-(4-dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine, isomer 2 (preparation 11, 145 mg, 0.67 mmol) provides the free amine of the title compound as a colorless oil (225 mg, 94%): MS (ES): m/z=358.1 (M+H)+; 1H NMR (CDCl3): δ 8.94 (d, 1H), 8.21 (m, 2H), 7.72 (t, 1H), 7.19 (d, 1H), 7.04 (m, 2H), 6.71 (m, 1H), 2.78 (m, 1H), 2.49 (m, 3H), 2.38 (s, 6H), 2.17 (m, 2H), 1.59 (m, 1H). Using a salt formation method similar to that in example 1 gives the dihydrochloride salt.

Sources & evidence

ORD record
ord-56848a3b50b84b9481b6c15059f2f722
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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