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Water → 6-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one

HRID 1597482
ノート
印刷プレビュー

反応式

HRID 1597482 の反応式
C([Si](C)(C)[C:6]1[N:10]([CH3:11])[C:9]([C:12]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)([OH:40])[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:18](=[O:27])[CH:17]=[C:16]3[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[C:35][Si](C)(C)C)[CH:29]=2)=[CH:8][N:7]=1)(C)(C)C.O>C1COCC1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:47][C:44]1[CH:45]=[CH:46][C:41]([C:12]([OH:40])([C:9]2[N:10]([CH3:11])[CH:6]=[N:7][CH:8]=2)[C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[N:19]([CH2:23][CH:24]2[CH2:26][CH2:25]2)[C:18](=[O:27])[CH:17]=[C:16]3[C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([C:34]#[CH:35])[CH:29]=2)=[CH:42][CH:43]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 962WaterHCID 185164406-[[2-(tert-Butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-(4-chloro-phenyl)-hydroxy-methyl]-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one

生成物 1

HCID 185164536-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one収率 54.9%

試薬・触媒・溶媒 2

HCID 70681
Tetrabutylammonium Chloride
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-[[2-(tert-Butyl-dimethyl-silanyl)-3-methyl-3H-imidazol-4-yl]-(4-chloro-phenyl)-hydroxy-methyl]-1-cyclopropylmethyl-4-(3-trimethylsilanylethynyl-phenyl)-1H-quinolin-2-one (4.50 g crude) in THF (100 mL) was treated with tetrabutylammonium chloride (1 M in THF, 10.0 mmol). The reaction mixture was stirred at room temperature for 12 hours, poured into H2O (200 mL), and extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with 1N HCl (100 mL), aqueous NaHCO3 (100 mL), and brine (100 mL), dried (MgSO4), filtered, and concentrated in vacuo to give a light green foam. Purification by flash column chromatography (silica, EtOAc:pet. ether:NH4OH 1:1:0.01) gave 6-[(4-Chloro-phenyl)-hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-1-cyclopropylmethyl-4-(3-ethynyl-phenyl)-1H-quinolin-2-one (1.82 g, 51%) as a yellow powder.

後処理

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with 1N HCl (100 mL), aqueous NaHCO3 (100 mL), and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a light green foam
  7. customPurification by flash column chromatography (silica, EtOAc:pet. ether:NH4OH 1:1:0.01)

出典と根拠

ORDレコード
ord-25347beb04c74058b0b48e1681f72fe9
出典データセット
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06294552B1

反応ノート

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