Ammonia → HCID 136377184, compound

HRID 1027305Notes

Reaction equation

HRID 1027305 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[N:10][NH:11][CH:12]=2)[CH:5]=[CH:4][C:3]=1[C:13]1[N:18]=[N:17][C:16]([N:19]2[CH2:23][C@@H:22]3[CH2:24][N:25](C(OC(C)(C)C)=O)[CH2:26][C@@H:21]3[CH2:20]2)=[CH:15][CH:14]=1.Cl.N>O1CCOCC1.CO>[CH2:20]1[C@@H:21]2[CH2:26][NH:25][CH2:24][C@@H:22]2[CH2:23][N:19]1[C:16]1[N:17]=[N:18][C:13]([C:3]2[CH:4]=[CH:5][C:6]([C:8]3[CH:9]=[N:10][NH:11][CH:12]=3)=[CH:7][C:2]=2[OH:1])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 136377185(3aR,6aS)-tert-butyl 5-(6-(2-hydroxy-4-(1H-pyrazol-4-yl)phenyl)pyridazin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

HCID 136377184HCID 136377184, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (3aR,6aS)-tert-butyl 5-(6-(2-hydroxy-4-(1H-pyrazol-4-yl)phenyl)pyridazin-3-yl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (75 mg, 0.167 mmol) in 1 mL of dioxane was added 4N HCl in dioxane (1 mL, 4.00 mmol). The reaction mixture was stirred at RT overnight, and then basified with 2N NH3 in MeOH to form a precipitate which was separated via centrifugation to provide a dark solid, 2-(6-((3aR,6aS)-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyridazin 3-yl)-5-(1H-pyrazol-4-yl)phenol (50 mg, 0.136 mmol, 82% yield) MS (M+1)=349.1.

Workup

  1. customto form a precipitate which
  2. customwas separated via centrifugation

Sources & evidence

ORD record
ord-6d36a63e48934441b3113086521350c5
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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