Cyclopropylamine → HCID 24995223, compound

HRID 558174Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([CH2:8][S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[O:20][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:18][N:17]=2)[CH:5]=[CH:4][N:3]=1.[CH:28]1([NH2:31])[CH2:30][CH2:29]1>>[CH:28]1([NH:31][C:2]2[CH:7]=[C:6]([CH2:8][S:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]3[O:20][C:19]([NH:21][C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)=[N:18][N:17]=3)[CH:5]=[CH:4][N:3]=2)[CH2:30][CH2:29]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 24993344HCID 24993344, compound

Product 1

HCID 24995223HCID 24995223, compoundYield 6%

Conditions

Temperature: 150 °C

Procedure

To 5-(2-(2-fluoropyridin-4-yl) methylthiophenyl)-N-phenyl-1,3,4-oxadiazol-2-amine (80 mg, 0.19 mmol; Compound 1-(48)) was added cyclopropylamine (200 μL) at room temperature and then the mixture was stirred at 150° C. for 2 hours. The reaction solution was concentrated under a reduced pressure and the residue was purified with a silica gel column chromatography (hexane/ethyl acetate) and to give 5.0 mg (6%) of the titled compound as a colorless solid.

Workup

concentrationThe reaction solution was concentrated under a reduced pressure
customthe residue was purified with a silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record: ord-b87097abbba348b798ff4420c480ddbd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063034B2

Reaction notes

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