Pyrrolidine → 3-Oxo-3-(1-pyrrolidinyl)-n-[3-(trifluoromethyl)phenyl]propanamide

HRID 1766359Notes

Reaction equation

HRID 1766359 reaction equation
[O:1]=[C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)[CH2:3][C:4]([O-:6])=O.[Li+].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.C(N(C(C)C)C(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O>[O:6]=[C:4]([N:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)[CH2:3][C:2]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:1]

Participants

7

Reactant 5

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23693664Lithium 3-oxo-3-{[3-(trifluoromethyl)phenyl]amino}propanoate

Product 1

HCID 211101313-Oxo-3-(1-pyrrolidinyl)-n-[3-(trifluoromethyl)phenyl]propanamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 35A (200 mg, 0.79 mmol), pyrrolidine (62 mg, 0.869 mmol), ethyldiisopropylamine (224 mg, 1.7 mmol), 1-hydroxy-1H-benzotriazol hydrate (129 mg, 0.95 mmol), 4-N,N-dimethylaminopyridine (1 mg), and 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide hydrochloride (197 mg, 1.03 mmol) in dimethyl formamide (8 ml) is stirred at room temperature overnight (18 h). The crude reaction mixture is purified directly by preparative RP-HPLC to afford a yellow solid.

Workup

  1. customThe crude reaction mixture
  2. customis purified directly by preparative RP-HPLC
  3. customto afford a yellow solid

Sources & evidence

ORD record
ord-ede7995e305b46fba9308fe66452104d
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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