Triethylamine → HCID 67327884, compound

HRID 1158669Notes

Reaction equation

HRID 1158669 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH:13]([CH:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=3)[CH3:15])[CH2:12][N:11]([C:27](Cl)=[O:28])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].CCN(CC)CC.[CH3:37][N:38]1[C:42]([CH2:43][NH2:44])=[CH:41][N:40]=[CH:39]1>C(Cl)Cl>[CH3:37][N:38]1[C:42]([CH2:43][NH:44][C:27]([N:11]2[CH2:12][CH:13]([CH:14]([O:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][N:18]=3)[CH3:15])[CH:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:10]2)=[O:28])=[CH:41][N:40]=[CH:39]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27954241-Methyl-5-aminomethylimidazoleHCID 86628182(3SR,4RS)-3-(3,4-Dichloro-phenyl)-4-[(SR)-1-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-pyrrolidine-1-carbonyl chloride

Product 1

HCID 67327884HCID 67327884, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3SR,4RS)-3-(3,4-dichloro-phenyl)-4-[(SR)-1-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-pyrrolidine-1-carbonyl chloride (30 mg, 0.064 mmol) in CH2Cl2 (3 mL) were added Et3N (0.015 mL, 0.11 mmol) and C-(3-Methyl-3H-imidazol-4-yl)-methylamine (commercially available) (8 mg, 0.070 mmol). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, CH2Cl2/MeOH 98/2) to yield 14 mg (40%) the title compound as a white solid. ES-MS m/e: 542.2 (M+H+).

Workup

  1. concentrationthe reaction mixture was concentrated under vacuo
  2. customdirectly purified by flash chromatography (SiO2, CH2Cl2/MeOH 98/2)

Sources & evidence

ORD record
ord-4e265383135f40e6be10a1d2d457dc9b
Source dataset
uspto-grants-2010_10
Patent number
US07812021B2

Reaction notes

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