Phosgene → HCID 66608155, compound

HRID 1810389Notes

Reaction equation

HRID 1810389 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][CH2:25][CH3:26])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH:28]([N:31]([CH:34]([CH3:36])C)[CH2:32]C)([CH3:30])C.C(Cl)(Cl)=[O:38].N1CCCC1>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:27])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH2:23][N:24]([CH2:25][CH3:26])[C:32]([N:31]2[CH2:28][CH2:30][CH2:36][CH2:34]2)=[O:38])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 66603748(2'-Ethylaminomethyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 66608155HCID 66608155, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2′-ethylaminomethyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.207 g, 0.54 mmol) and diisopropylethylamine (0.38 mL, 2.16 mmol) in CH2Cl2 (2 mL) at 0° C. was added phosgene (20% in toluene; 0.43 mL, 0.81 mmol), and the reaction was stirred for 2 hours. Pyrrolidine (0.13 mL, 1.62 mmol) was added, and the reaction was stirred at 0° C. for 30 minutes. The mixture was concentrated, and the residue was purified by silica gel chromatography (20-40% EtOAc in hexanes) to give the title compound.

Workup

  1. stirringthe reaction was stirred at 0° C. for 30 minutes
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel chromatography (20-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b8f2625aa0b1412093a192920c869db1
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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