Hydrochloric Acid → 3-Chloro-4-((4-fluorotetrahydro-2h-pyran-4-yl)methoxy)benzenesulfonamide

HRID 1043208ノート

反応式

HRID 1043208 の反応式
[F:1][C:2]1([CH2:8][OH:9])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1.[H-].[Na+].[Cl:12][C:13]1[CH:14]=[C:15]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:16]=[CH:17][C:18]=1F.Cl>O1CCCC1.ClCCl.CN(C)C=O>[Cl:12][C:13]1[CH:14]=[C:15]([S:20]([NH2:23])(=[O:21])=[O:22])[CH:16]=[CH:17][C:18]=1[O:9][CH2:8][C:2]1([F:1])[CH2:7][CH2:6][O:5][CH2:4][CH2:3]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75098833-Chloro-4-fluorobenzenesulfonamideHCID 56971676(4-Fluorooxan-4-yl)methanol

生成物 1

HCID 671267243-Chloro-4-((4-fluorotetrahydro-2h-pyran-4-yl)methoxy)benzenesulfonamide

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of EXAMPLE 296C (0.175 g) in tetrahydrofuran (5 ml) was added sodium hydride (0.209 g) and the reaction stirred at room temperature for 15 minutes. 3-Chloro-4-fluorobenzenesulfonamide (0.273 g) was added and the reaction stirred for 3 hours. To the thick suspension was added tetrahydrofuran (2 ml) and N,N-dimethylformamide (3 ml). The reaction was stirred for 3 hours at 60° C. then poured into dichloromethane (50 ml) and 1N aqueous HCl (50 ml). The organic layer was washed with brine (35 ml) dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (Reveleris 40 g) eluting with a gradient of 10-100% ethyl acetate/hexanes over 30 minutes (flow=40 ml/minute) gave the title compound.

後処理

  1. stirringthe reaction stirred for 3 hours
  2. stirringThe reaction was stirred for 3 hours at 60° C.
  3. washThe organic layer was washed with brine (35 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washSilica gel chromatography (Reveleris 40 g) eluting with a gradient of 10-100% ethyl acetate/hexanes over 30 minutes (flow=40 ml/minute)

出典と根拠

ORDレコード
ord-fc97992bcbbe4b7f96633f0072fddd68
出典データセット
uspto-grants-2013_10
特許番号
US08557983B2

反応ノート

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