Dimethylformamide → HCID 86595597, compound

HRID 1246468Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[S:14][C:13]([NH:15][C:16](=[O:18])[CH3:17])=[N:12][CH:11]=2)=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([NH:26][C:27](N1C=CC=N1)=[N:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:25])([CH3:22])([CH3:21])[CH3:20].CN(C)C=O>O1CCCC1>[C:16]([NH:15][C:13]1[S:14][C:10]([CH2:9][CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH:27]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[NH:26][C:24](=[O:25])[O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:3][CH:4]=2)=[CH:11][N:12]=1)(=[O:18])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

N-{5-[2-(4-Aminophenyl)ethyl]-1,3-thiazol-2-yl}acetamide (100 mg), N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine (119 mg), N,N-dimethylformamide (1 ml) and tetrahydrofuran (2 ml) were combined under nitrogen atmosphere. The reaction mixture was stirred at 50° C. for 5.5 hours. After cooled to room temperature, the reaction mixture was concentrated in vacuo. The residue was purified by preparative silica gel column chromatography with n-hexane/ethyl acetate (1:2) as an eluent to give di-tert-butyl {[(4-{2-[2-(acetylamino)-1,3-thiazol-5-yl]ethyl}phenyl)amino]methylidene}biscarbamate (93.9 mg) as a colorless solid.

Workup

temperatureAfter cooled to room temperature
concentrationthe reaction mixture was concentrated in vacuo
customThe residue was purified by preparative silica gel column chromatography with n-hexane/ethyl acetate (1:2) as an eluent

Sources & evidence

ORD record: ord-048764501c0f4fbf94b1b39bc0cefc47
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125901B2

Reaction notes

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