Sodium Hydroxide → HCID 117653190, compound

HRID 588394Notes

Reaction equation

HRID 588394 reaction equation
C([O:3][C:4]([C:6]1[N:10]([CH3:11])[N:9]=[CH:8][C:7]=1[C:12]1[CH:43]=[CH:42][C:15]([C:16]([N:18]([C@@H:29]2[CH2:34][CH2:33][CH2:32][N:31]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:30]2)[C:19]2[N:20]=[CH:21][CH:22]=[C:23]3[CH:27]=[CH:26][N:25]([CH3:28])[C:24]=23)=[O:17])=[CH:14][CH:13]=1)=[O:5])C.[OH-].[Na+]>CO>[C:38]([O:37][C:35]([N:31]1[CH2:32][CH2:33][CH2:34][C@@H:29]([N:18]([C:19]2[N:20]=[CH:21][CH:22]=[C:23]3[CH:27]=[CH:26][N:25]([CH3:28])[C:24]=23)[C:16]([C:15]2[CH:42]=[CH:43][C:12]([C:7]3[CH:8]=[N:9][N:10]([CH3:11])[C:6]=3[C:4]([OH:5])=[O:3])=[CH:13][CH:14]=2)=[O:17])[CH2:30]1)=[O:36])([CH3:41])([CH3:40])[CH3:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 117652846HCID 117652846, compound2×

Product 1

HCID 117653190HCID 117653190, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the compound from Step 2 (R)-tert-butyl 3-(4-(5-(ethoxycarbonyl)-1-methyl-1H-pyrazol-4-yl)-N-(1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)benzamido)piperidine-1-carboxylate (0.2 g, 0.34 mmol) in MeOH (10 mL) was added aqueous NaOH (2 N, 1.5 mL). The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure, and the pH was adjusted with 1N HCl until pH 4. The acidified mixture was extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure to deliver the title compound (0.18 g) as yellow oil which was used in the next step without purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionThe acidified mixture was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customwas used in the next step without purification

Sources & evidence

ORD record
ord-2b4477c9029b4209812993c35d555eeb
Source dataset
uspto-grants-2016_01
Patent number
US09227956B2

Reaction notes

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