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

HRID 1627384ノート

反応式

HRID 1627384 の反応式
[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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 78373Dimethylformamide dimethyl acetal触媒HCID 887Methanol溶媒HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-39c9d968a0c44caa80108bf40974754d
出典データセット
uspto-grants-2014_07
特許番号
US08785488B2

反応ノート

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