Ethyl Acetate → N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamide

HRID 877984Notes

Reaction equation

HRID 877984 reaction equation
FC(F)(F)C(O)=O.[CH3:8][NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH3:22].CCN(C(C)C)C(C)C.[F:32][C:33]([F:48])([F:47])[C:34]1[CH:35]=[C:36]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[C:37](Cl)=[O:38].CCOC(C)=O>C(Cl)Cl.CCCCCC>[CH3:8][N:9]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][C:15]=1[N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH3:22])[C:37](=[O:38])[C:36]1[CH:40]=[C:41]([C:43]([F:44])([F:45])[F:46])[CH:42]=[C:34]([C:33]([F:32])([F:47])[F:48])[CH:35]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 70663603Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3'-yl)-amine trifluoroacetic acid salt

Product 1

HCID 86670691N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamideYield 26%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

Methyl-(2-methyl-3,4,5,6-tetrahydro-2H[1,4′]bipyridinyl-3′-yl)-amine trifluoroacetic acid salt was dissolved in CH2Cl2 (2 mL) and treated with DIPEA (100 μL, 0.59 mmol) and 3,5-bis-trifluoromethylbenzoyl chloride (76 mg, 0.28 mmol, CAS RN 1271-19-8). The reaction mixture was loaded directly on a silica gel column and the title product (23 mg, 26% over two steps) was isolated by elution with 66% EtOAc in n-hexane. MS (ESI): m/z=445.9 [M+H]+.

Sources & evidence

ORD record
ord-9ee12cca3cbd4fb48d6ef395c28de5a9
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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