Sodium hydride → 5-Chloro-6-((4-(cyclopropyl(oxetan-3-yl)amino)cyclohexyl)methoxy)pyridine-3-sulfonamide

HRID 1036022노트

반응식

HRID 1036022 반응식
[CH:1]1([N:4]([CH:13]2[CH2:16][O:15][CH2:14]2)[CH:5]2[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.[H-].[Na+].[Cl:19][C:20]1[CH:21]=[C:22]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:23]=[N:24][C:25]=1Cl.[NH4+].[Cl-]>CN(C)C=O>[Cl:19][C:20]1[CH:21]=[C:22]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:23]=[N:24][C:25]=1[O:12][CH2:11][CH:8]1[CH2:7][CH2:6][CH:5]([N:4]([CH:1]2[CH2:2][CH2:3]2)[CH:13]2[CH2:16][O:15][CH2:14]2)[CH2:10][CH2:9]1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 67126731[4-[Cyclopropyl(oxetan-3-yl)amino]cyclohexyl]methanol

생성물 1

HCID 671267985-Chloro-6-((4-(cyclopropyl(oxetan-3-yl)amino)cyclohexyl)methoxy)pyridine-3-sulfonamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of EXAMPLE 329C (706 mg) in N,N-dimethylformamide (6 mL) was added NaH (60% in mineral oil, 300 mg). The mixture was stirred for 30 minutes, and then 5,6-dichloropyridine-3-sulfonamide (706 mg) was added. The mixture was stirred overnight. The mixture was poured over aqueous NH4Cl and extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with water, brine and dried over Na2SO4. After filtration and evaporation of the solvent the residue was loaded on a silica gel cartridge and eluted with 5 to 10% 7N NH3 in methanol in dichloromethane to provide the title compound.

후처리

  1. stirringThe mixture was stirred overnight
  2. extractionextracted with ethyl acetate (3×200 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of the solvent the residue
  6. washeluted with 5 to 10% 7N NH3 in methanol in dichloromethane

출처 및 근거

ORD 기록
ord-169c06902316441f98489248237c2d8e
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546399B2

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