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

HRID 574919ノート

反応式

HRID 574919 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-acf4b9f59786495abdfdcf14c2b4e06c
出典データセット
uspto-grants-2015_05
特許番号
US09034875B2

反応ノート

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