1-Hydroxybenzotriazole → 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamide

HRID 1665683ノート

反応式

HRID 1665683 の反応式
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[CH:20]=[C:19]([NH:21][C:22](=[O:27])[CH2:23][C:24]([OH:26])=O)[O:18][N:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([N:48]1[CH2:53][CH2:52][NH:51][CH2:50][CH2:49]1)=[O:47]>CN(C=O)C.O>[Br:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[C:46]([N:48]1[CH2:49][CH2:50][N:51]([C:24](=[O:26])[CH2:23][C:22]([NH:21][C:19]2[O:18][N:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:20]=2)=[O:27])[CH2:52][CH2:53]1)=[O:47]

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57875817N-(3-phenyl-isoxazol-5-yl)-malonamic acidHCID 66625832(2-Bromo-phenyl)-piperazin-1-yl-methanone hydrochloride

生成物 1

HCID 442316833-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamide収率 43.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (69.2 mg, 0.55 mmol) was added to a stirred solution of N-(3-phenyl-isoxazol-5-yl)-malonamic acid (45 mg, 0.18 mmol) in DMF (2 mL) followed by HOBt (29 mg, 0.22 mmol). After 2 minutes of stirring, (2-bromo-phenyl)-piperazin-1-yl-methanone hydrochloride (67 mg, 0.22 mmol) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 38.9 mg (43.22% Yield) of 3-[4-(2-bromo-benzoyl)-piperazin-1-yl]-3-oxo-N-(3-phenyl-isoxazol-5-yl)-propionamide. LC/MS [M+1]+: 497.07, 97.0%. 1H NMR: (300 MHz, DMSO-d6): δ 11.8 (bs, 1H), 7.92-7.8 (m, 2H), 7.5 (d, 1H), 7.6-7.3 (m, 6H), 6.8-6.7 (d, 1H), 3.8-3.4 (m, 8H), 3.24-3.04 (m, 2H).

後処理

  1. stirringstirring
  2. waitwas continued at ambient temperature overnight
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-db137e823b9a477d9af9d5844aee295d
出典データセット
uspto-grants-2011_10
特許番号
US08039463B2

反応ノート

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