2-Chloro-6-fluorobenzoyl chloride → HCID 69350870, compound

HRID 970755Notes

Reaction equation

HRID 970755 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[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]=[CH:9][CH:8]=[C:7]([F:11])[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 27365472-Chloro-6-fluorobenzoyl chlorideHCID 588523656-(4-Dimethylamino-cyclohex-1-enyl)-pyridin-2-ylamine

Product 1

HCID 69350870HCID 69350870, compoundYield 48%

Procedure

Using a method similar to example 1, using 2-chloro-6-fluoro-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 (82 mg, 48%): MS (ES): m/z=374 (M+H)+; 1H NMR (CD3OD): δ 8.15 (t, 1H), 7.57 (m, 3H), 7.34 (d, 1H), 7.20 (t, 1H), 6.71 (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-5613a211e42647ed809113d970026973
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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