Trifluoroacetic acid → Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3'-yl)-amine trifluoroacetic acid salt

HRID 877988Notes

Reaction equation

HRID 877988 reaction equation
[CH3:1][N:2]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH3:31])C(=O)C1C=C(C(F)(F)F)C=C(C(F)(F)F)C=1.[C:32]([OH:38])([C:34]([F:37])([F:36])[F:35])=[O:33]>C(Cl)Cl>[OH:38][C:32]([C:34]([F:37])([F:36])[F:35])=[O:33].[CH3:1][NH:2][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][C:24]=1[N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[CH3:31]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86670691N-Methyl-N-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl-3'-yl)-3,5-bis-trifluoromethyl-benzamide2×

Product 1

HCID 70663603Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3'-yl)-amine trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3′-yl)-carbamic acid tert-butyl ester (60 mg, 0.20 mmol, example 20, intermediate b) was stirred in a solution of TFA (300 μL) and CH2Cl2 (2 mL) for 1 h after which all volatiles were removed under reduced pressure to give crude methyl-(2-methyl-3,4,5,6-tetrahydro-2H-[1,4]bipyridinyl-3′-yl)-amine TFA salt. The crude TFA salt was dissolved in CH2Cl2 (2 mL) and treated with DIPEA (100 μL, 590 mmol) and 3,5-dichlorobenzoyl chloride (54 mg, 0.26 mmol, CAS RN 2905-62-6). The reaction mixture was loaded directly on a silica gel column and elution with 66% EtOAc in n-hexane gave the title product (12 mg, 16%). MS (ESI): m/z=378.0 [M+H]+.

Workup

  1. customwere removed under reduced pressure

Sources & evidence

ORD record
ord-5c711b786415443b9d66f7d041cfc89f
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

Loading…