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Sodium Hydroxide → N-[5-(4-{5-[(8aS)-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylmethyl]-1,3,4-oxadiazol-2-yl}-1H-indazol-6-yl)-2-(methyloxy)-3-pyridinyl]methanesulfonamide

HRID 520638
Notes
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Reaction equation

HRID 520638 reaction equation
[CH2:1]1[N:6]([CH2:7][C:8]2[O:12][C:11]([C:13]3[CH:21]=[C:20]([C:22]4[CH:23]=[C:24]([NH:30][S:31]([CH3:34])(=[O:33])=[O:32])[C:25]([O:28][CH3:29])=[N:26][CH:27]=4)[CH:19]=[C:18]4[C:14]=3[CH:15]=[N:16][N:17]4S(C3C=CC=CC=3)(=O)=O)=[N:10][N:9]=2)[CH2:5][CH2:4][N:3]2[CH2:44][CH2:45][CH2:46][C@@H:2]12.[OH-].[Na+]>O1CCOCC1>[CH2:1]1[N:6]([CH2:7][C:8]2[O:12][C:11]([C:13]3[CH:21]=[C:20]([C:22]4[CH:23]=[C:24]([NH:30][S:31]([CH3:34])(=[O:32])=[O:33])[C:25]([O:28][CH3:29])=[N:26][CH:27]=4)[CH:19]=[C:18]4[C:14]=3[CH:15]=[N:16][NH:17]4)=[N:10][N:9]=2)[CH2:5][CH2:4][N:3]2[CH2:44][CH2:45][CH2:46][C@@H:2]12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66693044N-[5-[4-{5-[(8aS)-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylmethyl]-1,3,4-oxadiazol-2-yl}-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide

Product 1

HCID 66695909N-[5-(4-{5-[(8aS)-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylmethyl]-1,3,4-oxadiazol-2-yl}-1H-indazol-6-yl)-2-(methyloxy)-3-pyridinyl]methanesulfonamideYield 34.7%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

N-[5-[4-{5-[(8aS)-Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-ylmethyl]-1,3,4-oxadiazol-2-yl}-1-(phenylsulfonyl)-1H-indazol-6-yl]-2-(methyloxy)-3-pyridinyl]methanesulfonamide (95 mg, 0.143 mmol) was dissolved in 1,4-dioxane (1 ml) and sodium hydroxide (1 ml, 0.143 mmol) was added. The mixture was stirred at room temperature for 1 h. The mixture was dried down under a stream of nitrogen and the residue partitioned between ethyl acetate (5 ml) and saturated ammonium chloride (2 ml). The organic layer was separated, dried by passing through a hydrophobic frit and the solvent removed in vacuo to give an orange oil. This was triturated with cyclohexane to give the title compound as an orange solid (26 mg).

Workup

  1. customThe mixture was dried down under a stream of nitrogen
  2. customthe residue partitioned between ethyl acetate (5 ml) and saturated ammonium chloride (2 ml)
  3. customThe organic layer was separated
  4. customdried
  5. customthe solvent removed in vacuo
  6. customto give an orange oil
  7. customThis was triturated with cyclohexane

Sources & evidence

ORD record
ord-393e559a52414060acb1256414a21503
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09326987B2

Reaction notes

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