Sodium borohydride → HCID 86714222, compound

HRID 925510Notes

Reaction equation

HRID 925510 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[C:28]([Cl:31])[N:29]=4)[N:24]=[CH:23][C:22]=3[C:32](OC)=[O:33])=[CH:16][C:15]=2[C:36]([F:39])([F:38])[F:37])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[Cl:31][C:28]1[N:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]=[CH:23][C:22]([CH2:32][OH:33])=[C:21]2[NH:20][C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:13][CH2:12]2)=[C:15]([C:36]([F:39])([F:37])[F:38])[CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86714221HCID 86714221, compound

Product 1

HCID 86714222HCID 86714222, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-((4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-3-(trifluoromethyl)phenyl)amino)-6-chloro-1,5-naphthyridine-3-carboxylate (0.565 g, 1.0 mmol) was added to ethanol (10 mL), to the system added sodium borohydride (0.228 g, 6 mmol) in batches, stirred at room temperature for 18 h. Ethanol was removed under reduced pressure, added 10 mL of water, and extracted with 80 mL of dichloromethane. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to give 0.568 g of a crude solid product. The solid was directly used in the next step.

Workup

  1. customEthanol was removed under reduced pressure
  2. additionadded 10 mL of water
  3. extractionextracted with 80 mL of dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d347fa119254d519da5b6e20a0d9daa
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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