AcOH THF water → 10a-[4-(2-hydroxyethoxy)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1753172Notes

Reaction equation

HRID 1753172 reaction equation
[Si]([O:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]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:19]2[C:20](=[O:27])[C:21]2[N:22]([CH:24]=[CH:25][CH:26]=2)[CH2:23]3)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C(O)(=O)C.C1COCC1.O>C(Cl)Cl>[OH:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]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:19]2[C:20](=[O:27])[C:21]2[N:22]([CH:24]=[CH:25][CH:26]=2)[CH2:23]3)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 21877175AcOH THF waterHCID 6737182410a-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

Product 1

HCID 5840638110a-[4-(2-hydroxyethoxy)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-oneYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10a-[4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethoxy)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (80 mg, 0.14 mmol) was treated with a 3:1:1 mixture of acetic acid/THF/water (2 mL). The solution was stirred at room temperature overnight. The mixture was then diluted with CH2Cl2 (20 mL) and washed with a saturated aqueous solution of NaHCO3 (3×6 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give a gummy solid that was purified by flash chromatography (Biotage SP4, 12 g silica column gradient 0-10% MeOH in CH2Cl2) to give 10a-[4-(2-hydroxyethoxy)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (109) (38 mg, yield 64%).

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3 (3×6 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a gummy solid
  6. customthat was purified by flash chromatography (Biotage SP4, 12 g silica column gradient 0-10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-c5328d9c6afd4a1390b2fe652370243e
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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