5-(Chloromethyl)-2-(trifluoromethyl)pyridine → HCID 11662235, compound
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:32]=[CH:31][C:6]([C:7]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([N:19]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)[C:20](=[O:22])[CH3:21])[CH2:11][C@@H:10]2[CH3:30])=[O:8])=[CH:5][CH:4]=1.FC(F)(F)C1C=CC(CCl)=CN=1>>[Cl:29][C:26]1[CH:25]=[CH:24][C:23]([N:19]([C@H:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]([C:7](=[O:8])[C:6]3[CH:5]=[CH:4][C:3]([C:2]#[N:1])=[CH:32][CH:31]=3)[C@@H:10]([CH3:30])[CH2:11]2)[C:20](=[O:22])[CH3:21])=[CH:28][CH:27]=1Participants
Procedure
N-{(2S,4R)-1-[4-(aminomethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was made following general procedure H, substituting 4-cyanobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. The rest of the procedure is followed as indicated in general procedure H to yield the corresponding nitrile, N-(4-chloro-phenyl)-N-[(2S,4R)-1-(4-cyano-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. N-(4-Chloro-phenyl)-N-[(2S,4R)-1-(4-cyano-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (225 mg, 0.51 mmol) was dissolved in ethanol (7 mL) and cobalt dichloride (0.079 g, 0.61 mmol) and NaBH4 (0.059 g, 1.57 mmol) were added and the mixture was stirred at room temperature for 2 h. The slurry was filtered, concentrated, and subjected to flash chromatography (1% NH4OH, 15% MeOH, EtOAc) to yield the title compound (188 mg, 83%) as a white solid. 1H-NMR (CDCl3) δ: 1.00-1.20 (m, 1H), 1.14 (s, 3H), 1.48 (bs, 2H), 2.02 (s, 3H), 2.20-2.36 (m, 1H), 3.79 (s, 2H), 4.73-4.83 (m, 1H), 5.35-5.70 (m, 1H), 6.49 (d, 1H), 6.89 (t, 1H), 7.11-7.29 (m, 8H), 7.37 (d, 2H).
Sources & evidence
- ORD record
- ord-4427dbe6f55d4b5a9b94c15c61ee6b54
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504508B2
Reaction notes
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