Lithium Hydroxide → HCID 49870068, compound

HRID 1631313Notes

Reaction equation

HRID 1631313 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33]CC)=[O:32])[CH2:27][CH2:26]3)=[O:24])=[C:16]2[N:15]=1.[Li+].[OH-]>C1COCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@H:9]1[CH2:13][CH2:12][CH2:11][N:10]1[C:14]1[CH:19]=[CH:18][N:17]2[N:20]=[CH:21][C:22]([C:23]([N:25]3[CH2:26][CH2:27][CH:28]([C:31]([OH:33])=[O:32])[CH2:29][CH2:30]3)=[O:24])=[C:16]2[N:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86664570HCID 86664570, compound

Product 1

HCID 49870068HCID 49870068, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(R)-ethyl 1-(5-(2-(2,5-di fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbonyl)piperidine-4-carboxylate (49 mg, 0.10 mmol) was dissolved in 1:1 THF/MeOH (1.0 mL) and 1M LiOH (0.20 mL, 0.20 mmol) was added. The mixture was stirred at ambient temperature for 2 hours and the reaction mixture was concentrated. The residue was diluted in water and the mixture acidified with 2N HCl. The mixture was extracted with DCM and EtOAc. The combined organics were washed with brine, dried with MgSO4, filtered and concentrated. The residue was triturated with hexanes and the resulting white suspension was concentrated to afford the final product (43 mg, 92% yield) as a white solid. MS (apci) m/z=456.1 (M+H).

Workup

  1. additionwas added
  2. concentrationthe reaction mixture was concentrated
  3. additionThe residue was diluted in water
  4. extractionThe mixture was extracted with DCM and EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was triturated with hexanes
  10. concentrationthe resulting white suspension was concentrated

Sources & evidence

ORD record
ord-b2d9ce6e498a448681ae96a2abed6d97
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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