Triethylamine → HCID 22660692, compound

HRID 1935705Notes

Reaction equation

HRID 1935705 reaction equation
Cl.[F:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[C:5](=[O:17])[O:6][C:7]12[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[C:18]1([C:24]2[CH:25]=[N:26][C:27]([NH:30][C:31](=O)[O:32]C3C=CC=CC=3)=[N:28][CH:29]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[F:2][C:3]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:4]=1[C:5](=[O:17])[O:6][C:7]12[CH2:12][CH2:11][N:10]([C:31]([NH:30][C:27]2[N:26]=[CH:25][C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:29][N:28]=2)=[O:32])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22660706HCID 22660706, compoundHCID 22660718HCID 22660718, compound

Product 1

HCID 22660692HCID 22660692, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-fluorospiro[isobenzofuran-1(3H),4′-piperidine]-3-one hydrochloride (150 mg), phenyl N-(5-phenyl-2-pyrimidinyl)carbamate (170 mg) and triethylamine (0.24 mL) in chloroform (2 mL) was stirred at 60° C. for 3 hours. The concentration of the reaction mixture left a residue, which was purified by column chromatography on silica gel (hexane/ethyl acetate/methanol=1/1/0˜8/8/1˜6/6/1) followed by recrystallization from ethyl acetate-hexane to give the subject compound (190 mg) as colorless crystals (melting point 247-249° C.).

Workup

  1. waitThe concentration of the reaction mixture left a residue, which
  2. customwas purified by column chromatography on silica gel (hexane/ethyl acetate/methanol=1/1/0˜8/8/1˜6/6/1)
  3. customfollowed by recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ff39e428667e49e3b352d83bd3a5cc36
Source dataset
uspto-grants-2002_05
Patent number
US06388077B1

Reaction notes

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