Water → HCID 53373304, compound

HRID 1753181Notes

Reaction equation

HRID 1753181 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[N:30]([C:31]([C:33]4[C:34]([CH3:38])=[N:35][O:36][CH:37]=4)=[O:32])[CH2:29][CH2:28][N:10]2[C:11](=[O:27])[C:12]2[N:13]([CH:15]=[C:16]([N:18]4[CH:22]=[C:21]([Si](C)(C)C)[N:20]=[N:19]4)[CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.O.C([O-])(O)=O.[Na+]>C(O)(=O)C.O.C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]23[N:30]([C:31]([C:33]4[C:34]([CH3:38])=[N:35][O:36][CH:37]=4)=[O:32])[CH2:29][CH2:28][N:10]2[C:11](=[O:27])[C:12]2[N:13]([CH:15]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[N:19]4)[CH:17]=2)[CH2:14]3)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 67370525HCID 67370525, compound

Product 1

HCID 53373304HCID 53373304, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Conditions

Temperature
60 °C

Procedure

10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-[4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (10.6 mg, 0.012 mmol) was dissolved in a mixture of acetic acid/water/THF (3:1:1; 1 mL). The mixture was stirred at 60° C. When the reaction was complete (48 hours; monitored by LCMS) water was added followed by a saturated aqueous solution of NaHCO3. The mixture was then extracted with EtOAc (3 times) and the organics washed with brine, dried (Na2SO4), filtrated and concentrated in vacuo. The resulting material was purified by flash chromatography (Silica gel, EtOAc/Hex 3:1 followed by 100% EtOAc) to give compound 10a-(4-methoxyphenyl)-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(1H-1,2,3-triazol-1-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (113) as a white solid (2.28 mg, yield 25%)

Workup

  1. additionwas added
  2. extractionThe mixture was then extracted with EtOAc (3 times)
  3. washthe organics washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe resulting material was purified by flash chromatography (Silica gel, EtOAc/Hex 3:1 followed by 100% EtOAc)

Sources & evidence

ORD record
ord-771858361ccd4d79a28710ed70508005
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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