Tetrahydrofuran → 1-methyl-1H-imidazole-4-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide

HRID 2234714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234714
[CH3:1][N:2]([CH3:47])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:15][CH:16]=2)[CH:8]=[CH:7][C:6]=1[NH:38][C:39]([C:41]1[N:42]=[CH:43][N:44]([CH3:46])[CH:45]=1)=[O:40])=[O:4].O1CCCC1.[OH-].[K+]>CO>[CH3:47][N:2]([CH3:1])[C:3]([C:5]1[CH:10]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:8]=[CH:7][C:6]=1[NH:38][C:39]([C:41]1[N:42]=[CH:43][N:44]([CH3:46])[CH:45]=1)=[O:40])=[O:4]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 577315531-methyl-1H-imidazole-4-carboxylic Acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide

Produkt 1

HCID 577314841-methyl-1H-imidazole-4-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amideAusbeute 20,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-Methyl-1H-imidazole-4-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (0.092 mmol) was dissolved in methanol (0.25 mL) and tetrahydrofuran (0.25 mL) and 50% w/v aqueous potassium hydroxide (0.1 mL) was added at 0° C. After 2 hours, the reaction was quenched by addition of acetic acid (0.5 mL). The mixture was redissolved in tetrahydrofuran and the insoluble salts were removed by filtration. The crude material was purified by preparative HPLC to afford 1-methyl-1H-imidazole-4-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-amide (9.2 mg, 20.2%, 2 steps).

Aufarbeitung

  1. additionwas added at 0° C
  2. customthe reaction was quenched by addition of acetic acid (0.5 mL)
  3. dissolutionThe mixture was redissolved in tetrahydrofuran
  4. customthe insoluble salts were removed by filtration
  5. customThe crude material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5135b7f342a3479a8e24c82c24b13ca7
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709645B2

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