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

HRID 1692232Notes

Reaction equation

HRID 1692232 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-228b304eddd94e489c5e176fc4891da5
Source dataset
uspto-grants-2012_04
Patent number
US08153814B2

Reaction notes

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