Dimethylformamide → HCID 178523896, compound

HRID 1466182

Reaction equation

C(N=C=NCCCN(C)C)C.[F:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][C:34]=1[F:35])[C:16]([NH:18][C:19](=S)[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)=[O:17].[NH2:36][C:37]1[CH:38]=[C:39]([OH:43])[CH:40]=[N:41][CH:42]=1.CN(C)C=O>C(OCC)(=O)C>[F:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][C:34]=1[F:35])[C:16](/[N:18]=[C:19](\[NH:36][C:37]1[CH:42]=[N:41][CH:40]=[C:39]([OH:43])[CH:38]=1)/[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1)=[O:17]

Participants

Conditions

Temperature: 65 °C

Procedure

N1-((Ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine (43 mg, 0.278 mmol), 3,4-difluoro-N-((3-(trifluoromethyl)phenyl)carbamothioyl)benzamide (100 mg, 0.278 mmol) and 5-aminopyridin-3-ol (31 mg, 0.278 mmol) and were combined in a glass vial and dry dimethylformamide (1.5 mL) was added. The vial was capped and the mixture was heated at 65° C. for 2 h. After cooling the mixture to room temperature, the mixture was diluted with ethyl acetate and washed with water then brine. The organic layer was evaporated onto silica gel and the product was purified by chromatography eluting with 50-100% ethyl acetate in hexanes to give (Z)-3,4-difluoro-N-(((5-hydroxypyridin-3-yl)amino)((3 (trifluoromethyl)phenyl)amino)methylene)benzamide as a colorless oil.

Workup

customThe vial was capped
temperatureAfter cooling the mixture to room temperature
washwashed with water
customThe organic layer was evaporated onto silica gel
customthe product was purified by chromatography
washeluting with 50-100% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-c4823aeb7e2c4781af49183a6e05a0a2
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000014B2

Linked notes

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