Lithium Hydroxide → HCID 86690697, compound

HRID 711371Notes

Reaction equation

HRID 711371 reaction equation
C([O:4][C@@H:5]([CH3:28])[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:26]3[C:25]4[N:24]=[C:23]([Cl:27])[CH:22]=[CH:21][C:20]=4[N:19]=[CH:18][C:17]=3[N:16]=[N:15]2)[CH2:10][CH2:9]1)=[O:7])(=O)C.[Li+].[OH-]>C1COCC1.CO>[Cl:27][C:23]1[CH:22]=[CH:21][C:20]2[N:19]=[CH:18][C:17]3[N:16]=[N:15][N:14]([CH:11]4[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C@@H:5]([OH:4])[CH3:28])[CH2:9][CH2:10]4)[C:26]=3[C:25]=2[N:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86690694HCID 86690694, compound

Product 1

HCID 86690697HCID 86690697, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-1-oxopropan-2-yl acetate (1.2 g, 2.97 mmol) in a mixture of THF (30 mL) and MeOH (30 mL), was added LiOH (650 mg, 14.9 mmol) drop-wise. The mixture was stirred at room temperature for 3 h. After concentration in vacuo, the residue was diluted with water and the pH was adjusted to 7 with 2N HCl. The resulting mixture was concentrated and the precipitate was collected by filtration, washed with H2O, and dried in vacuo to afford (S)-1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-2-hydroxypropan-1-one as yellow solid. The crude product was used in next step without further purification. (918 mg, yield 85.4%). MS (m/z): 361 (M+H)+.

Workup

  1. concentrationAfter concentration in vacuo
  2. additionthe residue was diluted with water
  3. concentrationThe resulting mixture was concentrated
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-953ad8059a3644c096ce499c2cd2f7c1
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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