HCID 178418361, compound → HCID 23155176, compound

HRID 1912778Notes

Reaction equation

HRID 1912778 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:30])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([C:26]([NH:28]O)=[NH:27])=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[CH:13][CH:12]=2)=[CH:4][C:3]=1[C:31]([F:34])([F:33])[F:32].[H][H]>CO.[C].[Pd]>[F:33][C:31]([F:32])([F:34])[C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:30])[NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[C:20](=[CH:21][C:22]([C:26]([NH2:28])=[NH:27])=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:2]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178513227HCID 178513227, compound

Product 1

HCID 23155176HCID 23155176, compoundYield 27.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 10 mL of methanol, 12 mg (0.025 mmol) of 1-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-N-hydroxy-1H-indole-5-carboxamidine was dissolved and the solution was subjected to hydrogenation catalytic reduction on 10% palladium carbon in a hydrogen atmosphere at room temperature for 14 hours. After removal of the palladium carbon by a membrane filter, the filtrate was concentrated under reduced pressure, and the obtained product was triturated from diethyl ether to obtain 3 mg (25%) of 1-{4-[3-(3-(trifluoromethyl)phenyl)-ureido]phenyl}-1H-indole-5-carboxamidine (Table 1, Compound No. 25).

Workup

  1. customAfter removal of the palladium carbon by a membrane
  2. filtrationfilter
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe obtained product was triturated from diethyl ether

Sources & evidence

ORD record
ord-fc634fdba292458b89c5455265eeafd7
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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