3-Aminobenzamide → 3-{[(4-Bromophenoxy)acetyl]amino}benzamide

HRID 1945386

반응식

HRID 1945386 반응식
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=1)[C:17]([NH2:19])=[O:18].Cl.C(NCCCN=C=NCC)C.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]([NH:13][C:14]2[CH:15]=[C:16]([CH:20]=[CH:21][CH:22]=2)[C:17]([NH2:19])=[O:18])=[O:10])=[CH:11][CH:12]=1

참가 물질

7

반응물 5

HCID 16453-AminobenzamideHCID 74657p-Bromophenoxyacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 866015281-(3-Ethylaminopropyl)-3-ethylcarbodiimide hydrochloride

생성물 1

HCID 173978023-{[(4-Bromophenoxy)acetyl]amino}benzamide수율 21.52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of (4-bromo-phenoxyacetic acid (392.5 mg, 1.8 mmol), 3-amino-benzamide (408.2 mg, 3.0 mmol), N-(3-ethylaminopropyl)-N′-ethyl carbodiimide HCl (EDC) (517.6 mg, 2.7 mmol) and 1-hydroxybenzotriazole (HOBt) (365.3 mg, 2.7 mmol) in DMF (18 mL) was added N,N-diisopropylethylamine, redistilled (DIPEA) (0.47 ml, 2.7 mmol). The mixture was stirred overnight and then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4 anh), and concentrated. The residue was purified by recrystallization from the mixture of Ethyl acetate and MeOH to give 3-[2-(4-bromo-phenoxy)acetyl-amino]-benzamide as a white solid (134.9 mg, 21.52% yield).

후처리

  1. distillationredistilled (DIPEA) (0.47 ml, 2.7 mmol)
  2. custompartitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4 anh)
  5. concentrationconcentrated
  6. customThe residue was purified by recrystallization from the mixture of Ethyl acetate and MeOH

출처 및 근거

ORD 기록
ord-2bf3b5ca4dc64704b75dad322be49c28
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394799B2

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