Methanol → 5-(13-Cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7h-indolo[2,1-a][2]benzazepin-6-yl)-1-ethyl-1h-pyrazole-4-carboxylic acid

HRID 1097807Notes

Reaction equation

HRID 1097807 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:39](=[O:47])[NH:40][S:41]([CH:44]([CH3:46])[CH3:45])(=[O:43])=[O:42])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]4[N:25]([CH2:26][CH3:27])[N:24]=[CH:23][C:22]=4[C:28]([O:30]CC)=[O:29])=[CH:18][C:17]4[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CO.[OH-].[Na+]>C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:39](=[O:47])[NH:40][S:41]([CH:44]([CH3:46])[CH3:45])(=[O:42])=[O:43])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]4[N:25]([CH2:26][CH3:27])[N:24]=[CH:23][C:22]=4[C:28]([OH:30])=[O:29])=[CH:18][C:17]4[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57948826Ethyl 5-(13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7h-indolo[2,1-a][2]benzazepin-6-yl)-1-ethyl-1h-pyrazole-4-carboxylate

Product 1

HCID 468931605-(13-Cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7h-indolo[2,1-a][2]benzazepin-6-yl)-1-ethyl-1h-pyrazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 5-(13-cyclohexyl-10-((isopropylsulfonyl)carbamoyl)-3-methoxy-7H-indolo[2,1-a][2]benzazepin-6-yl)-1-ethyl-1H-pyrazole-4-carboxylate was dissolved in THF (14 mL) and methanol (14 mL) then sodium hydroxide (15 mL, 15.00 mmol) (1.0N aqueous) was added to the reaction. The reaction was placed under a nitrogen atmosphere and stirred at room temperature for 16.5 hrs. The reaction was concentrated in vacuo using a rotary evaporator (bath temp equal to less than 26 C) then partitioned between ethyl acetate and 1.0N aqueous hydrochloric acid. The aqueous layer was extracted with ethyl acetate and the organic extracts combined, washed with brine and dried over magnesium sulfate. The organic solution was filtered and solvents removed in vacuo to give amorphous amber-orange solid (902 mg) after drying at room temperature in vacuo.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customa rotary evaporator (bath temp equal to less than 26 C)
  3. customthen partitioned between ethyl acetate and 1.0N aqueous hydrochloric acid
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationThe organic solution was filtered
  8. customsolvents removed in vacuo

Sources & evidence

ORD record
ord-2c11d508101f436680bfb71a3d4e5cd8
Source dataset
uspto-grants-2012_03
Patent number
US08143243B2

Reaction notes

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