Sodium borohydride → HCID 70929057, compound

HRID 447089Notes

Reaction equation

HRID 447089 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[C:21]([CH3:24])[C:22]=3[CH3:23])[CH2:13][C@H:12]2[CH3:33])=[N:9][CH:10]=1)=[O:4].[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([CH:25]([OH:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[C:21]([CH3:24])[C:22]=3[CH3:23])[CH2:13][C@H:12]2[CH3:33])=[N:9][CH:10]=1)=[O:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67178105HCID 67178105, compound

Product 1

HCID 70929057HCID 70929057, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To (R)-4-(6-benzoyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6 tetrahydro-2H-[1,2′]bipyrazinyl-5′-carboxylic acid methyl ester (8 mg, 0.017 mmol) in MeOH (2 mL) is added sodium borohydride (170 μg, 0.004 mmol) in 15 minutes and the reaction mixture is stirred at room temperature for 1 h. The reaction mixture is diluted with DCM and washed with NaHCO3 and water. The organic solvent is separated and the solvent is removed under reduced pressure. Purification by HPLC of the crude product with acetonitril in water (from 10% to 100% with 3% 1-propanol) at 220 nm wavelength detection provides the desired product as off white powder. (6 mg, 79%).

Workup

  1. washwashed with NaHCO3 and water
  2. customThe organic solvent is separated
  3. customthe solvent is removed under reduced pressure
  4. customPurification by HPLC of the crude product with acetonitril in water (from 10% to 100% with 3% 1-propanol) at 220 nm wavelength detection

Sources & evidence

ORD record
ord-2919d084e563404fa82330fe72f38aaa
Source dataset
uspto-grants-2013_07
Patent number
US08481542B2

Reaction notes

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