Dimethylamine → HCID 178485913, compound

HRID 1823766Notes

Reaction equation

C[O:2][C:3](=O)[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.[CH3:31][NH:32]C.N12CCCN=C1CCCC[CH2:35]2>CN(C)C=O>[CH:25]1([NH:24][C:21]2[CH:20]=[CH:19][C:18]([S:15]([O:14][C:12]3[CH:11]=[CH:10][C:8]4[NH:9][C:5]([N:4]([CH3:35])[C:3]([NH:32][CH3:31])=[O:2])=[N:6][C:7]=4[CH:13]=3)(=[O:17])=[O:16])=[CH:23][CH:22]=2)[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

Conditions

Temperature: 80 °C

Procedure

Title compound was obtained by reacting 10 mg of methyl-5-(4-cyclopentylaminophenylsulfonyloxy)benzimidazole-2-carbamate (example 19) with 50 μl dimethylamine (2.0 M in tetrahydrofuran) and 5 μl 1,8-diazabicyclo[5.4.0]undec-7-ene in 2 ml dimethylformamide 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 80° C. for 4 hours, and then cooled at room temperature. Compounds were put in an assay tube and dimethylformamide was evaporated in a JOUAN RC1010 evaporator. Compound was diluted in 0.5 ml dimethylsulfoxide for LC/MS trigged purification yielding 9 mg of the title compound (LC/MS analysis: retention time=3.35 min., mass spectrum: 444.29, [M+H]+).

Workup

customfor high pressure reaction
temperaturecooled at room temperature
customCompounds were put in an assay tube
customdimethylformamide was evaporated in a JOUAN RC1010 evaporator
additionCompound was diluted in 0.5 ml dimethylsulfoxide for LC/MS
custompurification

Sources & evidence

ORD record: ord-8442c588620b47188c09264c26f6fe93
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041668B2

Reaction notes

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