3,5-Bis(trifluoromethyl)benzoyl chloride → HCID 11641548, compound

HRID 1786009Notes

Reaction equation

HRID 1786009 reaction equation
FC(F)(F)[C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([C:34](F)(F)F)[CH:33]=1)[C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([Cl:18])=[CH:15][CH:16]=2)[C@H:11]([N:19]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:20](=[O:22])[CH3:21])[CH2:10][C@@H:9]1[CH3:30])=[O:7].F[C:41](F)(F)[C:42]1[CH:43]=[C:44]([CH:48]=[C:49](C(F)(F)F)[CH:50]=1)[C:45]([Cl:47])=O.ClC1C=CC(C(OC)=O)=C[N:59]=1.ClC1C=CC([N:75]([C@H]2C3C(=CC=CC=3)N(C(C3C=NC(CC)=CC=3)=O)[C@@H](C)C2)C(=O)C)=CC=1>>[Cl:18][C:14]1[CH:13]=[C:12]2[C:17](=[CH:16][CH:15]=1)[N:8]([C:6]([C:5]1[CH:31]=[N:59][C:33]([CH2:32][CH3:34])=[CH:3][CH:4]=1)=[O:7])[C@@H:9]([CH3:30])[CH2:10][C@H:11]2[N:19]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[C:20](=[O:22])[CH3:21].[CH2:42]([C:50]1[CH:49]=[CH:48][C:44]([CH2:45][Cl:47])=[CH:43][N:75]=1)[CH3:41]

Participants

6

Reactant 4

HCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 254249Methyl 6-chloropyridine-3-carboxylateHCID 57595404HCID 57595404, compoundHCID 57595460HCID 57595460, compound

Product 2

HCID 11641548HCID 11641548, compoundHCID 21698036HCID 21698036, compound

Procedure

N-{(2S,4R)-6-Chloro-1-[(6-ethylpyridin-3-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was prepared following the procedure described for N-{(2S,4R)-1-[3,5-bis(trifluoromethyl)benzoyl]-6-chloro-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide substituting 6-ethyl nicotinyl chloride for 3,5-bistrifluoromethyl benzoyl chloride. (6-Ethyl nicotinyl chloride was prepared in two steps from methyl 6-chloronicotinate as described in the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(6-ethylpyridin-3-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide).

Sources & evidence

ORD record
ord-433aac779362428ca7ba64aa1edae43c
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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