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

HRID 659097

Reaction equation

HRID 659097 reaction equation
[C:1]([C:9]1[O:13][C:12]([C:14]([OH:16])=O)=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=1)[CH3:18].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[CH:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH:29][C:14]([C:12]2[O:13][C:9]([C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[O:16])[CH:24]=1)[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 978253-Aminocinnamic acid ethyl esterHCID 28772555-Benzoylfuran-2-carboxylic acid

Product 1

HCID 684126103-{3-[(5-Benzoyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid (9) (48 mg, 0.22 mmol) was coupled to aniline (2) (43 mg, 0.22 mmol) using Method B, except that DIPEA (57 mg, 0.44 mmol) and DMF (0.5 mL) were used. The crude product was purified by preparative HPLC to give the title compound. Yield: 28 mg; LC-MS tr 41.54 min; MS (ES+) m/z 389 (M+H)

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-1a215cd9103e447a89e05584481b6c9e
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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