Lithium Hydroxide → HCID 58657578, compound

HRID 270744Notes

Reaction equation

HRID 270744 reaction equation
C[O:2][C:3](=[O:36])[C@H:4]([NH:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][C:26]2=[O:35])[CH2:21][CH2:20]1)=[O:18])[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[C:13]([CH3:15])[CH:14]=1)[NH:11][N:10]=[CH:9]2.[OH-].[Li+]>O1CCCC1.CO>[O:35]=[C:26]1[N:25]([CH:22]2[CH2:21][CH2:20][N:19]([C:17]([NH:16][C@H:4]([CH2:5][C:6]3[CH:7]=[C:8]4[C:12](=[C:13]([CH3:15])[CH:14]=3)[NH:11][N:10]=[CH:9]4)[C:3]([OH:36])=[O:2])=[O:18])[CH2:24][CH2:23]2)[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27]1

Participants

4

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 69201486HCID 69201486, compound

Product 1

HCID 58657578HCID 58657578, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A stirred solution of (R)-methyl-2-(4-(2-oxo-1,2-dihydroquinazolin-3 (4H)-yl)piperidine-1-carboxamido)-3 (7-methyl-1H-indazol-5-yl)propanoate (2.24 g, 4.57 mmol) in 1:1 tetrahydrofuran/methanol (25 mL) was cooled to 0° C. To this mixture was added 2N lithium hydroxide (11.4 mL, 22.8 mmol) in several portions. The reaction mixture was stirred at room temperature for 4.5 h, and then more lithium hydroxide solution (2 mL) was added. Stirring was continued for a further 3 h, and then the mixture was stored at 0° C. overnight. The mixture was concentrated in vacuo and the resulting residue was dissolved in water, cooled to 0° C., and treated with cold 6N hydrochloric acid at 0° C. until pH 2 was attained. The resulting precipitate was collected by filtration, washed with cold water and ether, and then dried under high vacuum overnight to give 1.53 g (80%) as a white solid. Mass spec.: 477.31 (MH)+. HPLC tR=1.87.

Workup

  1. stirringStirring
  2. waitwas continued for a further 3 h
  3. waitthe mixture was stored at 0° C. overnight
  4. concentrationThe mixture was concentrated in vacuo
  5. dissolutionthe resulting residue was dissolved in water
  6. temperaturecooled to 0° C.
  7. additiontreated with cold 6N hydrochloric acid at 0° C. until pH 2
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with cold water and ether
  10. customdried under high vacuum overnight
  11. customto give 1.53 g (80%) as a white solid

Sources & evidence

ORD record
ord-a5e826be20dc4669a781d77ac251bda1
Source dataset
uspto-grants-2008_11
Patent number
US07449586B2

Reaction notes

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