2-Bromobenzoyl chloride → HCID 69350334, compound
Reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([Cl:6])=[O:5].[CH3:11][N:12]([CH3:26])[CH:13]1[CH2:18][CH2:17][C:16]([C:19]2[N:24]=[C:23]([NH2:25])[CH:22]=[CH:21][CH:20]=2)=[CH:15][CH2:14]1>>[ClH:6].[ClH:6].[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:25][C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([C:16]2[CH2:17][CH2:18][CH:13]([N:12]([CH3:26])[CH3:11])[CH2:14][CH:15]=2)[N:24]=1)=[O:5]Participants
3
Procedure
Using a method similar to example 1, using 2-bromobenzoyl chloride (151 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 (63 mg, 34%): MS (ES): m/z=400 (M+H)+, 403 (M+3); 1H NMR (CD3OD): δ 8.30 (t, 1H), 7.69 (d, 2H), 7.67 (d, 1H), 7.49 (m, 3H), 6.78 (m, 1H), 3.55 (m, 1H), 2.87 (s, 6H), 2.73 (m, 4H), 2.37 (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-b729de464e0b4a448beab003e02c81f6
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312236B2
Reaction notes
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