Diisopropylethylamine → 3-{3-[(5-Phenoxy-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

HRID 659095

Reaction equation

HRID 659095 reaction equation
[O:1]([C:8]1[O:12][C:11]([C:13]([OH:15])=O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:18][C:19](=[O:29])[CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1)C.CCN(C(C)C)C(C)C>CN(C=O)C>[O:1]([C:8]1[O:12][C:11]([C:13]([NH:28][C:24]2[CH:23]=[C:22]([CH:21]=[CH:20][C:19]([OH:29])=[O:18])[CH:27]=[CH:26][CH:25]=2)=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 978253-Aminocinnamic acid ethyl esterHCID 28127905-Phenoxyfuran-2-carboxylic acid

Product 1

HCID 684136603-{3-[(5-Phenoxy-furan-2-carbonyl)-amino]-phenyl}-acrylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-phenoxy-2-furoic acid (3) (213 mg, 1.05 mmol) was coupled to aniline (2) (200 mg, 1.05 mmol) using Method B, except that DIPEA (270 mg, 2.09 mmol) and DMF (2 mL) were used to give the title compound. Yield: 178 mg, 96%; LC/MS tr 1.65 min; HPLC Purity: 95%; MS (ES+) m/z 378 (M+H)

Sources & evidence

ORD record
ord-b572637309d44c8aa5c4bf03177b49eb
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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