Sodium Hydroxide → 2-[1-[1-(4-Methoxy-2-methylphenyl)-6-methyl-2,3-dihydropyrrolo[2,3-b]pyridin-4-yl]pyrazol-3-yl]-1,2,5-thiadiazolidine 1,1-dioxide

HRID 32802Notes

Reaction equation

HRID 32802 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=3[CH3:19])[CH2:9][CH2:10][C:5]2=[C:4]([N:20]2[CH:24]=[CH:23][C:22]([N:25]3[S:29](=[O:31])(=[O:30])[N:28](C(OC)=O)[CH2:27][CH2:26]3)=[N:21]2)[CH:3]=1.[OH-].[Na+].C([O-])(O)=O.[Na+]>CO.C(Cl)Cl>[O:31]=[S:29]1(=[O:30])[NH:28][CH2:27][CH2:26][N:25]1[C:22]1[CH:23]=[CH:24][N:20]([C:4]2[CH:3]=[C:2]([CH3:1])[N:7]=[C:6]3[N:8]([C:11]4[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:12]=4[CH3:19])[CH2:9][CH2:10][C:5]=23)[N:21]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 11306561HCID 11306561, compound

Product 1

HCID 112476722-[1-[1-(4-Methoxy-2-methylphenyl)-6-methyl-2,3-dihydropyrrolo[2,3-b]pyridin-4-yl]pyrazol-3-yl]-1,2,5-thiadiazolidine 1,1-dioxideYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of example 5-1 (7.2 mg, 0.0144 mmol) in anh. MeOH (1 mL) and anh. CH2Cl2 (2 mL), at r.t., under N2, was added 25% NaOH (40 μL). The reaction mixture was stirred at r.t. for 30 min. It was then poured into sat.aq. NaHCO3 and CH2Cl2 was added. The phases were separated and the aqueous layer was further extracted with CH2Cl2 (2×10 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated to give the title compound (6.4 mg, quantitative yield) as a white solid.

Workup

  1. additionIt was then poured into sat.aq
  2. customThe phases were separated
  3. extractionthe aqueous layer was further extracted with CH2Cl2 (2×10 mL)
  4. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  5. filtrationthe solids were filtered
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-e8af4723cfc24a4badd9fd577fba28a5
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Reaction notes

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