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

HRID 1627384노트

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HRID 1627384 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 78373Dimethylformamide dimethyl acetal촉매HCID 887Methanol용매HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-39c9d968a0c44caa80108bf40974754d
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785488B2

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