Hydrochloric Acid → 1-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(2-methoxycarbonyl-2-methylpropoxy)indole-3-carbonitrile

HRID 1604668ノート

反応式

HRID 1604668 の反応式
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=5)[C:22]([C:30]#[N:31])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].S([O-])(=O)(=O)C.[C:37](=[O:40])([O-])[O-].[K+].[K+].Cl.CN(C)[CH:46]=[O:47]>O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:2][C:1]([C:37]([O:47][CH3:46])=[O:40])([CH3:4])[CH3:3])=[CH:26][CH:27]=5)[C:22]([C:30]#[N:31])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 85257MethanesulfonateHCID 196037114-Tert-butyl-2-{5-[(3-cyano-5-hydroxyindol-1-yl)methyl]benzofuran-2-yl}thiazole

生成物 1

HCID 196037631-{[2-(4-Tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(2-methoxycarbonyl-2-methylpropoxy)indole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Methansulfonyl chloride (0.13 ml) was added to the solution of methyl 3-hydroxy-2,2-dimethylpropionate (0.13 g) and triethylamine (0.28 ml) in dichloromethane over 20 minutes at -40° C. After 1 hour, the reaction mixture was allowed to warm to room temperature and concentrated under reduced pressure. The residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate, and the ethyl acetate layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give the corresponding mesylate (0.21 g). A mixture of 1-{[2-(4-tert-butylthiazol-2-yl]benzofuran-5-yl]methyl}-5-hydroxyindole-3-carbonitrile (0.35 g), the mesylate (0.21 g) and potassium carbonate (0.23 g) in N,N-dimethylformamide (5 ml) was stirred at 100° C. for 20 hours. After cooling, the reaction mixture was poured into water and made acidic with diluted hydrochloric acid. The resulting precipitates were collected by filtration and washed with water and subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and toluene. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(2-methoxycarbonyl-2-methylpropoxy)indole-3-carbonitrile (0.18 g).

後処理

  1. temperatureAfter cooling
  2. customThe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water
  5. washeluted with a mixture of ethyl acetate and toluene
  6. additionThe fractions containing the objective compounds
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-86dfcf72337e46f0a63b5d533c8fac13
出典データセット
uspto-grants-1999_11
特許番号
US05994378

反応ノート

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