Potassium Hydroxide → [2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester

HRID 2234677ノート

反応式

HRID 2234677 の反応式
[C:1]([O:5][C:6](=[O:53])[N:7]([CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[CH:28][N:27](S(C4C=CC(C)=CC=4)(=O)=O)[C:24]3=[N:25][CH:26]=2)=[CH:17][C:16]=1[C:48](=[O:52])[N:49]([CH3:51])[CH3:50])=[O:13])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>O1CCCC1.CO>[C:1]([O:5][C:6](=[O:53])[N:7]([CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[CH:28][NH:27][C:24]3=[N:25][CH:26]=2)=[CH:17][C:16]=1[C:48](=[O:52])[N:49]([CH3:50])[CH3:51])=[O:13])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 57731465[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 57731591[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester収率 92%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

[2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester (84 mg, 0.113 mmol) was dissolved in a solution of tetrahydrofuran (20 ml) and methanol (5 ml). A solution of aqueous potassium hydroxide (50% w/v, 5 ml) was added to the reaction mixture, and the combined mixture was allowed to stir for 1 hour at room temperature. The reaction mixture was quenched with sodium bicarbonate solution, and extracted with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (0-100% [10% methanol in ethyl acetate] in hexanes) to give 61 mg (92%) of [2-(3-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-ureido)-ethyl]-methyl-carbamic acid tert-butyl ester. MS: m/z 587.5 (M+H+).

後処理

  1. customThe reaction mixture was quenched with sodium bicarbonate solution
  2. extractionextracted with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (0-100% [10% methanol in ethyl acetate] in hexanes)

出典と根拠

ORDレコード
ord-ecd44705b942437dbfd0e4f5f5fe67b1
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

読み込み中…