[2-(1-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester → 1-(4-Chloro-3-(tri-fluoromethyl)phenyl)-3-{4-[4-(2-methylamino-ethoxy)-indol-1-yl]phenyl}urea hydrochloride

HRID 1912775Notes

Reaction equation

HRID 1912775 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[CH:15][N:16]2[C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([C:38]([F:41])([F:40])[F:39])[CH:32]=2)=[O:29])=[CH:23][CH:22]=1)C)(C)(C)C>C(OC(=O)C)C.Cl>[ClH:37].[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:28]([NH:27][C:24]2[CH:25]=[CH:26][C:21]([N:16]3[C:17]4[C:13](=[C:12]([O:11][CH2:10][CH2:9][NH:7][CH3:6])[CH:20]=[CH:19][CH:18]=4)[CH:14]=[CH:15]3)=[CH:22][CH:23]=2)=[O:29])=[CH:32][C:33]=1[C:38]([F:41])([F:39])[F:40]

Participants

3

Reactant 1

HCID 59725986[2-(1-{4-[3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester

Product 1

HCID 231549641-(4-Chloro-3-(tri-fluoromethyl)phenyl)-3-{4-[4-(2-methylamino-ethoxy)-indol-1-yl]phenyl}urea hydrochlorideYield 123.6%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

In 5 ml of a 4N hydrogen chloride ethyl acetate solution, 200 mg (0.33 mmol) of [2-(1-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-1H-indol-4-yloxy)ethyl]-methylcarbamic acid tert-butyl ester was dissolved and the solution was stirred at room temperature for 14 hours. The reaction solution was concentrated under reduced pressure, and then the obtained residue was triturated with ethyl acetate to obtain 110 mg (66%) of 1-(4-chloro-3-(tri-fluoromethyl)phenyl)-3-{4-[4-(2-methylamino-ethoxy)-indol-1-yl]phenyl}urea hydrochloride.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customthe obtained residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-fca6edf41bc14396a456c78aecfba7c2
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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