Triethylamine → 3-hydroxy-4-fluoro-N-cyclopropylbenzamide

反応式

[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=O.[CH:12]1([NH2:15])[CH2:14][CH2:13]1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C.O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([NH:15][CH:12]1[CH2:14][CH2:13]1)=[O:7]

参加物

反応物 5

HCID 8471Triethylamine

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

HCID 69828Cyclopropylamine

HCID 757711-Hydroxybenzotriazole

HCID 5936354-Fluoro-3-hydroxybenzoic acid

生成物 1

HCID 220191063-hydroxy-4-fluoro-N-cyclopropylbenzamide収率 61.5%

試薬・触媒・溶媒 2

実験手順

To a mixture of 3-hydroxy-4-fluorobenzoic acid (1.56 g, 10 mmol), cyclopropylamine (0.6 g, 10.5 mmol), triethylamine (1.02 g, 10 mmol) and HOBt (0.3 g, 2 mol) in DMF (10 mL) was added EDCI (2.0 g, 10.5 mmol) at RT. The mixture was stirred at RT overnight. The mixture was diluted with water and extracted with ethyl acetate (3×20 mL). The extract was washed with water and concentrated to afford 3-hydroxy-4-fluoro-N-cyclopropylbenzamide as a solid (1.2 g, 61.5%).