Sodium borohydride → HCID 59186318, compound

HRID 336410Notes

Reaction equation

HRID 336410 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=[O:26])=[CH:23][CH:22]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[BH4-].[Na+]>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[N:16]3[N:17]=[C:18]([NH:20][C:21]4[CH:22]=[CH:23][C:24]([CH2:25][OH:26])=[CH:27][CH:28]=4)[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59186516HCID 59186516, compound

Product 1

HCID 59186318HCID 59186318, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-(3-(methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzaldehyde (450 mg, 1.15 mmol) in tetrahydrofuran was added sodium borohydride (22 mg, 0.57 mmol) at 24° C. After 3 hr, the reaction mixture filtered through Celite. The solvent was removed in vacuo to provided the crude product which was purified by preparative thin layer chromatography to afford the desired product (300 mg, 67% yield). LCMS (ESI) m/z: 395.1.

Workup

  1. filtrationthe reaction mixture filtered through Celite
  2. customThe solvent was removed in vacuo
  3. customto provided the crude product which
  4. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-dac5d723b98b4c318476ce241fbef74e
Source dataset
uspto-grants-2014_11
Patent number
US08889673B2

Reaction notes

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