Cyclopropylamine → HCID 178522511, compound

HRID 1823767Notes

Reaction equation

CO[C:3](=[O:30])[NH:4][C:5]1[NH:6][C:7]2[CH:13]=[C:12]([O:14][S:15]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][CH:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH:11]=[CH:10][C:8]=2[N:9]=1.[CH:31]1([NH2:34])[CH2:33][CH2:32]1.N12CCCN=C1CCCCC2>CN1CCCC1=O.O1CCCC1>[CH:31]1([NH:34][C:3](=[O:30])[NH:4][C:5]2[NH:9][C:8]3[CH:10]=[CH:11][C:12]([O:14][S:15]([C:18]4[CH:19]=[CH:20][C:21]([NH:24][CH:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)=[CH:22][CH:23]=4)(=[O:16])=[O:17])=[CH:13][C:7]=3[N:6]=2)[CH2:33][CH2:32]1

Participants

Conditions

Temperature: 60 °C

Procedure

10 mg of methyl-5-(4-cyclopentylaminophenylsulfonyloxy)benzimidazole-2-carbamate (example 19) were combined with 25 μl cyclopropylamine and 10 μl 1,8-diazabicyclo[5.4.0]undec-7-ene in 2 ml N-methylpyrrolidone/tetrahydrofuran (0.8/1.2) in a 24 well Inox plate for high pressure reaction. The reaction mixture was put under a 10 Bars argon pressure and then heated to 60° C. for 40 hours, and then cooled to room temperature. Compounds were put in an assay tube, tetrahydrofuran was evaporated under reduced pressure and compound in N-methylpyrrolidone was directly purified by LC/MS trigged purification yielding 8.7 mg title compound. (LC/MS analysis: retention time=3.66 min., mass spectrum: 456.36, [M+H]+).

Workup

temperaturecooled to room temperature
customCompounds were put in an assay tube
customtetrahydrofuran was evaporated under reduced pressure and compound in N-methylpyrrolidone
customwas directly purified by LC/MS
custompurification

Sources & evidence

ORD record: ord-17c47578c6af40dcb12f36c01073b0f6
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041668B2

Reaction notes

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