Lithium Hydroxide → HCID 58406298, compound

HRID 1753200Notes

Reaction equation

HRID 1753200 reaction equation
CC1C(C([O:9][C:10]2[CH:18]=[C:17]3[N:12]([CH2:13][C:14]4([C:31]5[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=5)[N:22]([C:23]([C:25]5[C:26]([CH3:30])=[N:27][O:28][CH:29]=5)=[O:24])[CH2:21][CH2:20][N:15]4[C:16]3=[O:19])[N:11]=2)=O)=CON=1.[OH-].[Li+]>C1COCC1.CO>[CH3:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([C:14]23[N:22]([C:23]([C:25]4[C:26]([CH3:30])=[N:27][O:28][CH:29]=4)=[O:24])[CH2:21][CH2:20][N:15]2[C:16](=[O:19])[C:17]2[N:12]([NH:11][C:10](=[O:9])[CH:18]=2)[CH2:13]3)=[CH:36][CH:35]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67369874HCID 67369874, compound

Product 1

HCID 58406298HCID 58406298, compoundYield 38.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-5-oxo-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrazolo[1,5-d]pyrazin-7-yl 3-methyl-1,2-oxazole-4-carboxylate (120 mg, 0.23 mmol) in THF (1 mL) and methanol (1 mL) was added an aqueous solution of lithium hydroxide (0.1 M, 0.3 mL, 0.3 mmol). The mixture was stirred at room temperature until completion (2 h, monitored by LCMS). The solution was concentrated in vacuo and the residue partitioned between CH2Cl2 and 5% HCl (aq). The organic layer was separated and the aqueous layer further extracted with CH2Cl2. The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography using the Biotage SP4 (12 g cartridge, 0-10% methanol in CH2Cl2, 15 CV) to give 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrazolo[1,5-d]-pyrazine-5,7(8H)-dione (155) (36 mg, 38%).

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customthe residue partitioned between CH2Cl2 and 5% HCl (aq)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer further extracted with CH2Cl2
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-b3ea6707473347aa817e69cb2563a37c
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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