1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-4-fluorobenzamide

HRID 625785

반응식

HRID 625785 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.N.CO>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

참가 물질

7

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27249674-Fluoroanthranilic acidHCID 21705897Ammonia methanol

생성물 1

HCID 102410042-Amino-4-fluorobenzamide수율 72.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To solution of 2-amino-4-fluorobenzoic acid (4.0 g, 25.8 mmol) in degassed DMF (50 mL) were added HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.94 g, 31 mmol) and 2N NH3/MeOH (18 mL, 36.1 mmol). The solution was stirred at rt for 48 h, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 2-amino-4-fluorobenzamide as a solid (2.89 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 6.28 (m, 1H), 6.44 (m, 1H), 6.90 (br s, 2H), 7.08 (m, 1H), 7.58 (m, 1H), 7.71 (br d, 1H).

후처리

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-1a734152fcc34c9aafc56644849d0576
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308207B2

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