Sodium borohydride → N'-(3,5-difluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide

HRID 1627384Notes

Reaction equation

HRID 1627384 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:11]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:13])=[O:12])[CH:5]=[C:6]([F:10])[C:7]=1[CH:8]=[O:9].[BH4-].[Na+]>CO.CC#N.COC(OC)N(C)C>[F:10][C:6]1[CH:5]=[C:4]([S:11]([N:14]=[CH:15][N:16]([CH3:18])[CH3:17])(=[O:12])=[O:13])[CH:3]=[C:2]([F:1])[C:7]=1[CH2:8][OH:9]

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 86662257N'-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide

Product 1

HCID 66740347N'-(3,5-difluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamideYield 46.4%

Reagents, catalysts & solvents 3

HCID 78373Dimethylformamide dimethyl acetalCatalystHCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N′-(3,5-difluoro-4-formylphenylsulfonyl)-N,N-dimethylformimidamide (171 g, 619 mmol) in MeOH (1 L) was added NaBH4 (23.4 g, 619 mmol) at 0° C. After 1 h, the reaction mixture was concentrated, neutralized to pH 6 with 1N HCl, and extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4 and evaporated in vacuo. To a solution of this residue in CH3CN (1 L) was added N,N-dimethylformamide dimethylacetal (166 mL, 1.24 mmol, 2 eq). The solution was evaporated in vacuo and then purified by chromatography (silica, DCM/EtOAc, 1:1) to give N′-(3,5-difluoro-4-(hydroxymethyl)phenylsulfonyl)-N,N-dimethylformimidamide (80 g). 1H NMR (400 MHz, CDCl3) δ 8.10 (s, 1H), 7.45-7.40 (m, 2H), 4.8 (d, J=3.6 Hz), 3.17 (s, 3H), 3.05 (s, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with EtOAc
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe solution was evaporated in vacuo
  7. custompurified by chromatography (silica, DCM/EtOAc, 1:1)

Sources & evidence

ORD record
ord-39c9d968a0c44caa80108bf40974754d
Source dataset
uspto-grants-2014_07
Patent number
US08785488B2

Reaction notes

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