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

HRID 1945386

反応式

HRID 1945386 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2bf3b5ca4dc64704b75dad322be49c28
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

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