Lithium Hydroxide → HCID 67471034, compound

HRID 1426969Notes

Reaction equation

HRID 1426969 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26]([O:28]CC)=[O:27])=[C:19]3[N:18]=2)=[CH:10][C:9]([F:31])=[CH:8][N:7]=1.[OH-].[Li+]>C1COCC1.CO>[NH2:2][CH2:3][CH2:4][CH2:5][C:6]1[C:11]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]2[CH:22]=[CH:21][N:20]3[N:23]=[CH:24][C:25]([C:26]([OH:28])=[O:27])=[C:19]3[N:18]=2)=[CH:10][C:9]([F:31])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86691752HCID 86691752, compound

Product 1

HCID 67471034HCID 67471034, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To (R)-ethyl 5-(2-(2-(3-aminopropyl)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate hydrochloride (160 mg, 0.356 mmol) in THF/MeOH (2 mL/1 mL) was added lithium hydroxide (1.1 mL, 2.20 mmol). The reaction mixture was heated to 70° C. for 5 hours, then concentrated under reduced pressure. Water (10 mL) was added and the mixture washed with Et2O (2×5 mL), then neutralized with HCl (1M) to pH=4. The aqueous solution was extracted with DCM (2×10 mL). The organic extract was dried with Na2SO4, filtered and concentrated under reduced pressure to give the crude desired product (16.0 mg, 11.7% yield). MS (apci) m/z=385.0 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater (10 mL) was added
  3. washthe mixture washed with Et2O (2×5 mL)
  4. extractionThe aqueous solution was extracted with DCM (2×10 mL)
  5. extractionThe organic extract
  6. dry with materialwas dried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-053745e51e6d407e8b8429431eb43aea
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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