Bromide ion → Formate

HRID 572354Notes

Reaction equation

HRID 572354 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[C:32]([O-])([O-:34])=[O:33].[K+].[K+].Br[CH2:39][CH2:40][CH2:41][N+:42]([CH3:45])([CH3:44])[CH3:43].[Br-]>CN(C=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:39][CH2:40][CH2:41][N+:42]([CH3:45])([CH3:44])[CH3:43])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[CH:32]([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 259Bromide ionHCID 11430Potassium CarbonateHCID 1511463-bromo-N,N,N-trimethyl-1-propanaminiumHCID 529122224-[(2s,4r)-1-Acetyl-4-[(4-Chlorophenyl)amino]-2-Methyl-1,2,3,4-Tetrahydroquinolin-6-Yl]benzoic Acid

Product 2

HCID 283FormateYield 19%HCID 709819153-{[(4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}phenyl)carbonyl]oxy}-N,N,N-trimethyl-1-propanaminium

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-{(2S,4R)-1-Acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoic acid (for a preparation see Intermediate 18) (150 mg, 0.345 mmol) was dissolved in DMF (3 mL) and K2CO3 (47.7 mg, 0.345 mmol) then 3-bromo-N,N,N-trimethyl-1-propanaminium, bromide (90 mg, 0.345 mmol) were added. The resulting mixture was stirred at room temperature overnight, whereupon the reaction mixture was concentrated in vacuo and purified by MDAP (formate) to give 3-{[(4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}phenyl)carbonyl]oxy}-N,N,N-trimethyl-1-propanaminium, formate (41 mg, 0.064 mmol, 19% yield) as a yellow oil. LCMS (Formate, 2 min), Rt=0.86 min, MH+=534.

Workup

  1. concentrationwas concentrated in vacuo
  2. custompurified by MDAP (formate)

Sources & evidence

ORD record
ord-bdde8edf6b62448fbbb5666993dc638d
Source dataset
uspto-grants-2015_05
Patent number
US09029395B2

Reaction notes

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