HCID 11643000, compound → HCID 11534114, compound

HRID 2301569Notes

Reaction equation

HRID 2301569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([NH:22][CH2:23][CH:24]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]2)(=[O:21])=[O:20])[C:13]=1[OH:37])=[O:10]>Cl.O1CCOCC1>[ClH:18].[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([S:19]([NH:22][CH2:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)(=[O:20])=[O:21])[C:13]=1[OH:37])=[O:10]

Participants

4

Reactant 1

HCID 11643000HCID 11643000, compound

Product 1

HCID 11534114HCID 11534114, compoundYield 131.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(2-bromophenyl)-N′-[3-[N″-[(1-tert-butoxycarbonylpiperidin-4-yl)methyl]aminosulfonyl]-4-chloro-2-hydroxyphenyl] urea (27 mg, 0.044 mmol) in 1.0 mL of 4.1 N HCl in 1,4-dioxane was stirred at room temperature for 10 min. The mixture was concentrated. Recrystallization from acetone and hexane gave desired product (16 mg, 65%). LC-MS (m/z) 519.2 (M+).

Workup

  1. concentrationThe mixture was concentrated
  2. customRecrystallization from acetone and hexane

Sources & evidence

ORD record
ord-c1725d377f8f48529936582c19cb634b
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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