Sodium hydride → 5-Chloro-6-((2-oxo-1-oxa-3-azaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

HRID 2040333ノート

反応式

HRID 2040333 の反応式
[OH:1][CH2:2][CH:3]1[CH2:13][CH2:12][C:6]2([O:10][C:9](=[O:11])[NH:8][CH2:7]2)[CH2:5][CH2:4]1.[H-].[Na+].[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[N:21][C:22]=1Cl>O1CCCC1.CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]([S:24]([NH2:27])(=[O:26])=[O:25])[CH:20]=[N:21][C:22]=1[O:1][CH2:2][CH:3]1[CH2:13][CH2:12][C:6]2([O:10][C:9](=[O:11])[NH:8][CH2:7]2)[CH2:5][CH2:4]1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 47309215,6-Dichloropyridine-3-sulfonamideHCID 575765318-(Hydroxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

生成物 1

HCID 671266985-Chloro-6-((2-oxo-1-oxa-3-azaspiro[4.5]decan-8-yl)methoxy)pyridine-3-sulfonamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of EXAMPLE 385C (325 mg, 1.755 mmol) in a mixture of tetrahydrofuran (16 mL) and N,N-dimethylformamide (8 mL) was added sodium hydride (281 mg, 7.02 mmol) and the mixture was stirred for 30 minutes. 5,6-Dichloropyridine-3-sulfonamide (389 mg) was added and the reaction was stirred for 42 hours. The reaction was quenched with water (5 mL) and concentrated. The residue was diluted with 75% brine (200 mL) and extracted with methylene chloride (3×200 mL). The organics were dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel and eluted with a 1, 5, and 10% methanol in methylene chloride step gradient to provide the title compound.

後処理

  1. stirringthe reaction was stirred for 42 hours
  2. customThe reaction was quenched with water (5 mL)
  3. concentrationconcentrated
  4. additionThe residue was diluted with 75% brine (200 mL)
  5. extractionextracted with methylene chloride (3×200 mL)
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel
  10. washeluted with a 1, 5, and 10% methanol in methylene chloride step gradient

出典と根拠

ORDレコード
ord-59556d39da234405892d362ded1f5e35
出典データセット
uspto-grants-2013_11
特許番号
US08580794B2

反応ノート

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