Methanol → HCID 178432256, compound

HRID 74441Notes

Reaction equation

HRID 74441 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].CO.[NH2:9][C:10]1[N:14]([C:15]2[CH:24]=[CH:23][C:18]3[NH:19][C:20]([CH3:22])=[N:21][C:17]=3[CH:16]=2)[N:13]=[CH:12][C:11]=1[C:25]([C:27]1[N:28](S(C2C=CC=CC=2)(=O)=O)[C:29]2[C:34]([CH:35]=1)=[CH:33][C:32]([CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[CH:31][CH:30]=2)=[O:26].O.N>O>[NH2:9][C:10]1[N:14]([C:15]2[CH:24]=[CH:23][C:18]3[NH:19][C:20]([CH3:22])=[N:21][C:17]=3[CH:16]=2)[N:13]=[CH:12][C:11]=1[C:25]([C:27]1[NH:28][C:29]2[C:34]([CH:35]=1)=[CH:33][C:32]([CH2:36][N:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1)=[CH:31][CH:30]=2)=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 12896473Azane;hydrateHCID 178432255HCID 178432255, compound

Product 1

HCID 178432256HCID 178432256, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cesium carbonate (1.29 g) was added to a methanol solution (20 ml) of [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-5-morpholin-4-ylmethyl-1H-indol-2-yl)-methanone (110 mg), and stirred at room temperature for 16 hours. Then, water (5 ml) and ammonia water (3 ml) were added to the reaction mixture and stirred for three hours. The reaction mixture was concentrated under reduced pressure. Water was added to the resulting residue. After ethyl acetate extraction, the extract was washed with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100) to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(5-morpholin-4-ylmethyl-1H-indol-2-yl)-methanone (33 mg).

Workup

  1. stirringstirred for three hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added to the resulting residue
  4. extractionAfter ethyl acetate extraction
  5. washthe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe desiccant was removed by filtration
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 20/100)

Sources & evidence

ORD record
ord-6503c8e5f0c348c8ab6ce243682eeac0
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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