Pyridine → HCID 76803837、化合物

HRID 1191111ノート

反応式

HRID 1191111 の反応式
Cl.[CH3:2][O:3][NH2:4].N1C=CC=CC=1.[C:11]([C:14]1[CH:39]=[CH:38][C:17]([CH2:18][NH:19][C:20]2[C:30]3[CH2:29][CH2:28][N:27]([C:31](=[O:36])[C:32]([F:35])([F:34])[F:33])[CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][C:21]=2[Cl:37])=[CH:16][CH:15]=1)(=O)[CH3:12]>C(O)C>[Cl:37][C:21]1[CH:22]=[CH:23][C:24]2[CH2:25][CH2:26][N:27]([C:31](=[O:36])[C:32]([F:35])([F:33])[F:34])[CH2:28][CH2:29][C:30]=2[C:20]=1[NH:19][CH2:18][C:17]1[CH:16]=[CH:15][C:14]([C:11](=[N:4][O:3][CH3:2])[CH3:12])=[CH:39][CH:38]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 59828832HCID 59828832、化合物

生成物 1

HCID 76803837HCID 76803837、化合物収率 83%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Add O-methylhydroxylamine hydrochloride (10 mg, 0.12 mmol) and pyridine (0.02 mL, 0.24 mmol) to a solution of 6-(4-acetyl-benzylamino)-7-chloro-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine (50 mg, 0.12 mmol) in ethanol (10 mL). Heat the mixture to reflux for 1.5 h. Remove the solvent in vacuo and partition the residue between DCM and 0.1N aqueous HCl. Dry the organic phase over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (95:5 to 1:1 gradient over 30 min). Concentrate in vacuo to obtain 7-chloro-6-[4-(1-methoxyimino-ethyl)-benzylamino]-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a colorless oil (45 mg, 83%). MS (ES+) m/z: 454 (M+H)+.

後処理

  1. temperatureHeat the mixture
  2. temperatureto reflux for 1.5 h
  3. customRemove the solvent in vacuo
  4. custompartition the residue between DCM and 0.1N aqueous HCl
  5. dry with materialDry the organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify by chromatography on silica gel eluting with hexane/EtOAc (95:5 to 1:1 gradient over 30 min)
  9. concentrationConcentrate in vacuo

出典と根拠

ORDレコード
ord-c36702fed40445eda2d318b0f4330aaa
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

反応ノート

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