Hydrogen chloride-ethyl acetate → HCID 23155033, compound

HRID 1912769Notes

Reaction equation

HRID 1912769 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=3)=[O:25])=[CH:19][C:18]=1[F:38])[CH:12]=[CH:11]2)(C)(C)C.C(OC(=O)C)C.Cl>C(OCC)(=O)C>[ClH:33].[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([C:34]([F:37])([F:36])[F:35])[CH:28]=3)=[O:25])=[CH:19][C:18]=1[F:38])[CH:12]=[CH:11]2

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 59725917HCID 59725917, compound

Product 1

HCID 23155033HCID 23155033, compoundYield 178%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In 2 mL of ethyl acetate, 104 mg (0.18 mmol) of (1-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]-2-fluorophenyl}-1H-indol-5-yl)carbamic acid tert-butyl ester was dissolved, and 2 mL of a 4N hydrogen chloride ethyl acetate solution was added thereto and the mixture solution was stirred at room temperature for one hour. The reaction solution was concentrated and the obtained product was triturated with ethyl acetate to obtain 80 mg (86%) of 1-[4-(5-aminoindol-1-yl)-3-fluorophenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride (Table 1, Compound No. 17).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe obtained product was triturated with ethyl acetate

Sources & evidence

ORD record
ord-18921e7329fa4ab1b0818b2ed5759a5e
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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