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 2234714Notes

Reaction equation

HRID 2234714 reaction equation
[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]

Participants

5

Reactant 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

Product 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}-amideYield 20.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5135b7f342a3479a8e24c82c24b13ca7
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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