3-Aminocinnamic acid ethyl ester → 3-{3-[(Dibenzofuran-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

HRID 659103Notes

Reaction equation

HRID 659103 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14]([OH:16])=O.[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]>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:2]2[CH:3]=[CH:4][C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=2)=[O:16])[CH:24]=1)[CH3:18]

Participants

4

Reactant 2

HCID 978253-Aminocinnamic acid ethyl esterHCID 4174048-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-carboxylic acid

Product 1

HCID 684136723-{3-[(Dibenzofuran-2-carbonyl)-amino]-phenyl}-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid (18) (50 mg, 0.24 mmol) was coupled to aniline (2) (54 mg, 0.28 mmol) using Method D, except that DMF (1 mL) was used. The product was further purified by trituration in DCM/heptane to give the title compound. Yield: 46 mg, 51%; LC-MS tr 1.70 min; HPLC Purity: 97-100%; MS (ES+) m/z 386 (M+H)

Workup

  1. customThe product was further purified by trituration in DCM/heptane

Sources & evidence

ORD record
ord-b2c3063bdbde41079b807c139c24d1af
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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