Sodium Hydroxide → HCID 86662645, compound

HRID 38861Notes

Reaction equation

HRID 38861 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]([CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1.[OH-].[Na+]>C(O)(C)C.O>[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]([CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86662640HCID 86662640, compound

Product 1

HCID 86662645HCID 86662645, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

N-(2-Chloro-5-{1-[(4-methylphenyl)sulfonyl]-4-[5-(4-morpholinylmethyl)-1,3,4-oxadiazol-2-yl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (52 mg, 0.081 mmol) was placed in isopropanol (3 ml) and 2M sodium hydroxide (1 ml, 2.0 mmol) added. The mixture was stirred at room temperature overnight and blown to dryness under a stream of nitrogen. The mixture was dissolved in water (10 ml) and washed with dichloromethane (10 ml). The organic layer was acidified by the addition of 2M hydrochloric acid and the solvent removed. The residue was purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound (8 mg).

Workup

  1. washwashed with dichloromethane (10 ml)
  2. additionThe organic layer was acidified by the addition of 2M hydrochloric acid
  3. customthe solvent removed
  4. customThe residue was purified by Mass Directed Automated Preparative HPLC (Method B)

Sources & evidence

ORD record
ord-b423792b73df4545992cbe1e9ffd2096
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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