Cyclopropylamine → HCID 16722953, compound

HRID 1983157Notes

Reaction equation

HRID 1983157 reaction equation
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]([C:19]4[C:20]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)=[N:21][O:22][C:23]=4[CH3:24])=[N:17][N:18]=3)=[CH:10][CH:9]=2)=[O:7])[CH:5]=[CH:4]N=C1.[CH:31]1(N)CC1>O1CCCC1>[CH:5]1([NH:1][C:6](=[O:7])[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]([C:19]4[C:20]([C:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)=[N:21][O:22][C:23]=4[CH3:24])=[N:17][N:18]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:31]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 67215374HCID 67215374, compound

Product 1

HCID 16722953HCID 16722953, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of imidazol-1-yl-{4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenyl}-methanone (200 mg, 0.50 mmol) in tetrahydrofuran (2 mL) was added cyclopropylamine (37 mg, 0.65 mmol) and the mixture was stirred for 3 h at 80° C. After cooling to ambient temperature the resulting suspension was concentrated. Purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20) afforded the title compound (149 mg, 77%) as a white solid. MS: m/e=387.2 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature the resulting suspension
  2. concentrationwas concentrated
  3. customPurification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20)

Sources & evidence

ORD record
ord-e470bb806aea4fd7ac794d66dde89189
Source dataset
uspto-grants-2009_06
Patent number
US07541372B2

Reaction notes

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