Sodium Hydroxide → HCID 86662646, compound

HRID 38876Notes

Reaction equation

HRID 38876 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3S(C3C=CC(C)=CC=3)(=O)=O)=[C:15]([C:32]3[O:33][C:34]([CH3:37])=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1.[OH-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][NH:19]3)=[C:15]([C:32]3[O:33][C:34]([CH3:37])=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86662641HCID 86662641, compound

Product 1

HCID 86662646HCID 86662646, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-(2-chloro-5-{4-(5-methyl-1,3,4-oxadiazol-2-yl)-1-[(4-methylphenyl)sulfonyl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (16 mg, 0.029 mmol) and 2M sodium hydroxide (1 ml, 2.0 mmol) were placed in isopropanol (5 ml) and the mixture stirred at room temperature overnight. The solvent was removed and the residue partitioned between water (5 ml) and dichloromethane (5 ml). The aqueous was acidified to ˜pH 1 with 2M hydrogen chloride, then extracted with dichloromethane (20 ml). The organic layer was concentrated to give the title compound as a white solid (10 mg).

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between water (5 ml) and dichloromethane (5 ml)
  3. extractionextracted with dichloromethane (20 ml)
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-c5c692eec63440c9a7035cf113f07452
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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