Hydrochloric Acid → 4-{2-[2-(Azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluoro-N-1,3-thiazol-4-ylbenzenesulfonamide

HRID 46269Notes

Reaction equation

HRID 46269 reaction equation
[N:1]1([CH2:5][C:6]2[CH:11]=[C:10]([C:12]3[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:13]=3[O:14][C:15]3[C:20]([F:21])=[CH:19][C:18]([S:22]([N:25]([C:33]4[N:34]=[CH:35][S:36][CH:37]=4)C(=O)OC(C)(C)C)(=[O:24])=[O:23])=[C:17]([F:38])[CH:16]=3)[CH:9]=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1.Cl>ClCCl.O1CCOCC1>[N:1]1([CH2:5][C:6]2[CH:11]=[C:10]([C:12]3[CH:42]=[C:41]([Cl:43])[CH:40]=[CH:39][C:13]=3[O:14][C:15]3[C:20]([F:21])=[CH:19][C:18]([S:22]([NH:25][C:33]4[N:34]=[CH:35][S:36][CH:37]=4)(=[O:23])=[O:24])=[C:17]([F:38])[CH:16]=3)[CH:9]=[CH:8][N:7]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59436494tert-Butyl [(4-{2-[2-(azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate

Product 1

HCID 468419354-{2-[2-(Azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluoro-N-1,3-thiazol-4-ylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl [(4-{2-[2-(azetidin-1-ylmethyl)pyridin-4-yl]-4-chlorophenoxy}-2,5-difluorophenyl)sulfonyl]1,3-thiazol-4-ylcarbamate, (Preparation 878, 0.325 g, 0.0005 mol) was dissolved in dichloromethane (3 mL) then 4 molar hydrogen chloride in 1,4-dioxane (3 mL) was added. The reaction was stirred at room temperature for 18 hours. The reaction was concentrated in vacuo and the crude product purified by preparative HPLC to give the title compound.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-86454fc9125149e1b421dc453cdc9e39
Source dataset
uspto-grants-2013_09
Patent number
US08541588B2

Reaction notes

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