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1-Hydroxybenzotriazole hydrate → 1-[4-Chloro-2-(trifluoromethyl)phenyl]-5-[2-(dimethylamino)-2-oxoethyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide

HRID 238962
ノート
印刷プレビュー

反応式

HRID 238962 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14](=[O:26])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)[CH:10]=[C:9]2[CH2:27][C:28](O)=[O:29])=[C:4]([C:31]([F:34])([F:33])[F:32])[CH:3]=1.O.ON1C2C=CC=CC=2N=N1.[CH3:46][NH:47][CH3:48].C1COCC1>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([CH2:27][C:28]([N:47]([CH3:48])[CH3:46])=[O:29])=[CH:10][C:11]([C:14]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[O:26])=[C:12]2[CH3:13])=[C:4]([C:31]([F:33])([F:32])[F:34])[CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 27960291-Hydroxybenzotriazole hydrateHCID 22320367Dimethylamine tetrahydrofuranHCID 67376656(1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid

生成物 1

HCID 452791841-[4-Chloro-2-(trifluoromethyl)phenyl]-5-[2-(dimethylamino)-2-oxoethyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide収率 54%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of the above (1-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-4-{[4-(methylsulfonyl)phenyl]carbamoyl}-1H-pyrrol-2-yl)acetic acid (30 mg, 0.518 mmol) in DMF (0.58 mL), 1-hydroxybenzotriazole monohydrate (18 mg, 0.12 mmol) and hydrochloric acid 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide (23 mg, 0.12 mmol) were successively added, and the mixture was stirred at room temperature for 1 hour. Thereafter, a 2M dimethylamine/THF solution was added to the mixture, and the mixture was stirred overnight. After the reaction, it was diluted with ethyl acetate, and the organic layer was washed with 1M hydrochloric acid, water and saturated brine. Thereafter, it was dried with sodium sulfate, filtration was carried out, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (17 mg, 54%).

後処理

  1. stirringthe mixture was stirred overnight
  2. customAfter the reaction, it
  3. washthe organic layer was washed with 1M hydrochloric acid, water and saturated brine
  4. dry with materialThereafter, it was dried with sodium sulfate, filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-32ca8c75f39c49a292aee21de54de583
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08642640B2

反応ノート

読み込み中…

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