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 2234677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234677
[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]

Komponenten

5

Edukt 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

Produkt 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 esterAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ecd44705b942437dbfd0e4f5f5fe67b1
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709645B2

Notizen zur Reaktion

Wird geladen…