Hydrochloric Acid → 1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl)-ethane-1,2-diol

HRID 1480000Notes

Reaction equation

HRID 1480000 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[N:24][C:23]([C:26](=[O:29])[CH2:27][OH:28])=[CH:22][N:21]=3)[C@H:16]([CH3:30])[CH2:15]2)=[C:10]([CH3:31])[C:9]=1[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CCO>[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[N:24][C:23]([CH:26]([OH:29])[CH2:27][OH:28])=[CH:22][N:21]=3)[C@H:16]([CH3:30])[CH2:15]2)=[C:10]([CH3:31])[C:9]=1[CH3:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 591915351-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl)-2-hydroxy-ethanone

Product 1

HCID 591915951-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl)-ethane-1,2-diolYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-5′-yl)-2-hydroxy-ethanone (example 114, 110 mg, 0.25 mmol) and EtOH (20 ml) is added NaBH4 (14 mg, 0.38 mmol) at 0° C. The mixture is warmed up to room temperature and stirred for 3 h. The reaction solution is acidified with 3N HCl to pH˜7 and the organic solvent is removed. The residue is dissolved in saturated NaHCO3 solution and extracted with DCM. The organic layer is concentrated to afford the title compound (96 mg, 91%) as a white solid.

Workup

  1. customthe organic solvent is removed
  2. dissolutionThe residue is dissolved in saturated NaHCO3 solution
  3. extractionextracted with DCM
  4. concentrationThe organic layer is concentrated

Sources & evidence

ORD record
ord-1aa2939c013847c68d4022f37d6d9138
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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