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

HRID 1043208노트

반응식

HRID 1043208 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-fc97992bcbbe4b7f96633f0072fddd68
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557983B2

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