Lithium Hydroxide → HCID 53373031, compound

HRID 1753139Notes

Reaction equation

HRID 1753139 reaction equation
[Li+].[OH-].CC1C(C([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]34[N:37]([C:38]([C:40]5[C:41]([CH3:45])=[N:42][O:43][CH:44]=5)=[O:39])[CH2:36][CH2:35][N:20]3[C:21](=[O:34])[C:22]3[N:23]([CH:25]=[C:26]([C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)[CH:27]=3)[CH2:24]4)=[CH:15][CH:14]=2)=O)=CON=1.CO.CC#N>[Cl-].[Na+].O>[OH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]23[N:37]([C:38]([C:40]4[C:41]([CH3:45])=[N:42][O:43][CH:44]=4)=[O:39])[CH2:36][CH2:35][N:20]2[C:21](=[O:34])[C:22]2[N:23]([CH:25]=[C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)[CH:27]=2)[CH2:24]3)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 21959252Acetonitrile methanolHCID 67368508HCID 67368508, compound

Product 1

HCID 53373031HCID 53373031, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

Aqueous LiOH solution (1M)(0.75 mg, 0.018 mmol) was added to a solution of 4-{1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-5-oxo-7-(pyridin-3-yl)-2,3-dihydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]-pyrazin-10a(10H)-yl}benzyl 3-methyl-1,2-oxazole-4-carboxylate (9.6 mg, 0.016 mmol) in a mixture MeOH/CH3CN (2 mL) and stirred at room temperature for 3 h. Brine (1 mL) was added and the resultant mixture was extracted with EtOAc (3×1 mL). The organic layers were combined, dried (MgSO4) and concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4 gradient 0-10% MeOH in EtOAc, 10CV and hold 10CV). The compound 10a-[4-(hydroxymethyl)phenyl]-1-[(3-methyl-1,2-oxazol-4-yl)carbonyl]-7-(pyridin-3-yl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (95) was isolated as a white solid (2.8 mg, yield 37%).

Workup

  1. extractionthe resultant mixture was extracted with EtOAc (3×1 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give a residue that
  5. customwas purified by flash chromatography (Biotage SP4 gradient 0-10% MeOH in EtOAc, 10CV and hold 10CV)

Sources & evidence

ORD record
ord-f8aee9893c864d43a3be78deb55d3340
Source dataset
uspto-grants-2015_10
Patent number
US09163029B2

Reaction notes

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