Formic Acid → HCID 57819985, compound

HRID 1714173Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=O)=[CH:8][CH:7]=1.[F:15][C:16]([F:26])([F:25])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]#[C-:24])=[CH:19][CH:18]=1.[O:27]1[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][NH2:35])[CH2:29][CH2:28]1.[CH:36](O)=[O:37].C[OH:40]>>[CH3:1][O:2][C:3](=[O:14])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([N:35]([CH:36]=[O:37])[CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][O:27][CH2:28][CH2:29]2)[C:24](=[O:40])[NH:23][C:20]2[CH:19]=[CH:18][C:17]([C:16]([F:25])([F:26])[F:15])=[CH:22][CH:21]=2)=[CH:8][CH:7]=1

Participants

Reactant 5

HCID 284Formic Acid

HCID 887Methanol2×

HCID 4082852-Morpholinoethylamine

HCID 27594124-(Trifluoromethyl)phenyl isocyanide

HCID 53401287Methyl 3-(4-formylphenyl)-2-propenoate

Product 1

HCID 57819985HCID 57819985, compoundYield 50.2%

Procedure

A solution of 4-formylcinnamic acid methyl ester (3.66 g, 19.2 mmol), 4-(trifluoromethyl)-phenyl isocyanide (3.32 g, 19.2 mmol), 2-morpholinoethylamine (2.50 g, 19.2 mmol) and formic acid solution in methanol (12.9 mL, 1.5M) in methanol (9 mL) was stirred at 80 degrees Celcius for 8 hours. After solvent removal, the crude product was directly purified by flash column chromatography over silica gel (dichloromethane/methanol, 100:1 to 20:1, v:v) to yield the desired product (5 g, 50.2%). MS: calc'd 520 (MH+) exp 520 (MH+).

Workup

customAfter solvent removal
customthe crude product was directly purified by flash column chromatography over silica gel (dichloromethane/methanol, 100:1 to 20:1, v:v)

Sources & evidence

ORD record: ord-f0cef49ace294342951db7bf6b203204
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795315B2

Reaction notes

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