Sodium Hydroxide → 5-(4-(azetidin-3-yloxy)-3-methoxyphenyl)-2-(4-chlorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one

HRID 554843ノート

反応式

HRID 554843 の反応式
C(OC([N:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([C:22]3[S:26][C:25]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[N:24][C:23]=3[CH2:34][CH:35](OC)OC)=[O:21])=[CH:15][C:14]=2[O:40][CH3:41])[CH2:9]1)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1>[NH:8]1[CH2:11][CH:10]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH:35]=[CH:34][C:23]4[N:24]=[C:25]([C:27]5[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=5)[S:26][C:22]=4[C:20]3=[O:21])=[CH:15][C:14]=2[O:40][CH3:41])[CH2:9]1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 674612343-(4-{[2-(4-Chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 249907925-(4-(azetidin-3-yloxy)-3-methoxyphenyl)-2-(4-chlorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one収率 94.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
95 °C

実験手順

Dissolve 3-(4-{[2-(4-chloro-phenyl)-4-(2,2-dimethoxy-ethyl)-thiazole-5-carbonyl]-amino}-2-methoxy-phenoxy)-azetidine-1-carboxylic acid tert-butyl ester (18.9 g, 31.28 mmol) and p-toluenesulfonic acid monohydrate (19.7 g, 103.56 mmol) in dry toluene (460 mL) and stir mechanically at 95° C. overnight. Cool the reaction mixture and add 1 N NaOH. Stir the mixture vigorously at room temperature for one hour. Extract the aqueous layer with CH2Cl2 (2×700 mL). Combine the organic portions, wash with brine (700 mL), dry over MgSO4, and filter. Concentrate the filtrate in vacuo to give 13.0 g (85%) of the title compound. ES/MS m/z (35Cl) 440.0 [M+1]+.

後処理

  1. temperatureCool the reaction mixture
  2. stirringStir the mixture vigorously at room temperature for one hour
  3. extractionExtract the aqueous layer with CH2Cl2 (2×700 mL)
  4. washCombine the organic portions, wash with brine (700 mL)
  5. dry with materialdry over MgSO4
  6. filtrationfilter
  7. concentrationConcentrate the filtrate in vacuo

出典と根拠

ORDレコード
ord-bfce355c0e59407989f400e77292b2dc
出典データセット
uspto-grants-2011_11
特許番号
US08049013B2

反応ノート

読み込み中…