Hexane → HCID 66977211, compound

HRID 712230Notes

Reaction equation

HRID 712230 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5]1.CCN(C(C)C)C(C)C.[Br:24][C:25]1[CH:26]=[N:27][C:28](Cl)=[N:29][CH:30]=1.CCCCCC>CCO>[Br:24][C:25]1[CH:26]=[N:27][C:28]([N:6]2[CH2:7][CH2:8][C:4]([C:3]([F:2])([F:13])[F:14])([C:9]([O:11][CH3:12])=[O:10])[CH2:5]2)=[N:29][CH:30]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 669769163-Trifluoromethyl-pyrrolidine-3-carboxylic acid methyl ester hydrochloride

Product 1

HCID 66977211HCID 66977211, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3-(trifluoromethyl)pyrrolidine-3-carboxylate hydrochloride (0.32 g, 1.36 mmol) in EtOH (10.0 mL) was added DIPEA (1.1 mL, 6.79 mmol) at rt and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (0.26 g, 1.36 mmol). The reaction was heated up to 70° C. for 1 h. After reaction completion (by TLC), the solvent was evaporated and the crude residue purified over 60-120 M silica-gel using 10.0% EtOAc:hexane to obtain the desired product as a yellow solid (0.30 g, 63% yield). MS: 354.02 [M+H]+.

Workup

  1. temperatureThe reaction was heated up to 70° C. for 1 h
  2. customAfter reaction completion (by TLC)
  3. customthe solvent was evaporated
  4. customthe crude residue purified over 60-120 M silica-gel

Sources & evidence

ORD record
ord-94dcfc86a5f44c47b1a50da24678a3e3
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…