Formic Acid → HCID 57820116, compound
Reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]=O)=[CH:20][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]([F:39])([F:38])[C:30]1[CH:35]=[CH:34][C:33]([N+:36]#[C-:37])=[CH:32][CH:31]=1.[O:40]1[CH2:45][CH2:44][N:43]([CH2:46][CH2:47][NH2:48])[CH2:42][CH2:41]1.[CH:49](O)=[O:50].C[OH:53]>>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:26])/[CH:16]=[CH:17]/[C:18]1[CH:19]=[CH:20][C:21]([CH:24]([N:48]([CH:49]=[O:50])[CH2:47][CH2:46][N:43]2[CH2:44][CH2:45][O:40][CH2:41][CH2:42]2)[C:37](=[O:53])[NH:36][C:33]2[CH:32]=[CH:31][C:30]([C:29]([F:38])([F:39])[F:28])=[CH:35][CH:34]=2)=[CH:22][CH:23]=1)([CH3:3])([CH3:2])[CH3:4]Participants
6
Procedure
A solution of (E)-{2-[3-(4-formyl-phenyl)-acryloylamino]-phenyl}-carbamic acid tert-butyl ester (1.10 g, 3.00 mmol), 4-(trifluoromethyl)-phenyl isocyanide (520 mg, 3.00 mmol), 2-morpholinoethylamine (391 mg, 3.00 mmol) and formic acid solution in methanol (2.0 mL, 1.5M) in methanol (1.0 mL) was stirred at 80 degrees Celcius for 4 hours. After solvent removal, the crude product was directly purified by flash column chromatography over silica gel (dichloromethane/methanol, 100:1 to 10:1, v:v) to yield the desired product (730 mg, 35%). MS: calc'd 696 (MH+) exp 696 (MH+).
Workup
- customAfter solvent removal
- customthe crude product was directly purified by flash column chromatography over silica gel (dichloromethane/methanol, 100:1 to 10:1, v:v)
Sources & evidence
- ORD record
- ord-8cf3bcf2b1734185859c81e3f088cf4a
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07795315B2
Reaction notes
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