Methylamine → HCID 58189164, compound

HRID 1423132Notes

Reaction equation

HRID 1423132 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16]([C:24]([F:27])([F:26])[F:25])=[N:17]3)[CH2:8][C@@H:7]1[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)C.[CH3:36][NH2:37].[C-]#N.[Na+]>CCO>[CH2:28]([C@H:7]1[CH2:8][N:9]([C:12]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]3[C:13]=2[CH:14]=[CH:15][C:16]([C:24]([F:27])([F:25])[F:26])=[N:17]3)[CH2:10][CH2:11][N:6]1[CH2:5][C:4]([NH:37][CH3:36])=[O:3])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8929Sodium CyanideHCID 66824790HCID 66824790, compound

Product 1

HCID 58189164HCID 58189164, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of [(S)-2-Benzyl-4-(8-methoxy-2-trifluoromethyl-quinolin-5-yl)-piperazin-1-yl]-acetic acid ethyl ester in a ˜33% methylamine solution in EtOH (5 mL) was treated with catalytic amount of sodium cyanide and allowed to stir for 48 h. The reaction mixture was then evaporated, washed with water and air dried to afford the title compound as a yellow solid (68 mg, 63%). LC/MS (Method B) 2.82 min, [M+1]+ 472.

Workup

  1. customThe reaction mixture was then evaporated
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-b4dc9c9f01db4c1d96d7b3b32aa5bc79
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

Loading…