Hydrochloric Acid → HCID 23154946, compound

HRID 1912772Notes

Reaction equation

HRID 1912772 reaction equation
[Cl:1][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](=[C:21]([O:26]C(=O)C)[CH:22]=[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].[OH-].[Na+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[C:25]4[C:20](=[C:21]([OH:26])[CH:22]=[CH:23][CH:24]=4)[CH:19]=[CH:18]3)=[CH:13][CH:12]=2)=[O:30])=[CH:4][C:3]=1[C:31]([F:34])([F:32])[F:33]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59725932HCID 59725932, compound

Product 1

HCID 23154946HCID 23154946, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 3 mL of tetrahydrofuran, 60 mg (0.12 mmol) of acetic acid 1-(4-[3-(4-chloro-3-(trifluoromethyl)phenyl)-ureido]phenyl)-1H-indol-4-yl ester was dissolved, and 1 mL of a 1N sodium hydroxide aqueous solution was added thereto and the mixture solution was stirred at room temperature for two hours. The reaction solution was neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried and then concentrated under reduced pressure, and the obtained residue was recrystallized from ethyl acetate to obtain 17 mg (31%) of 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-[4-(4-hydroxyindol-1-yl)phenyl]urea (Table 1, Compound No. 19) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with a saturated sodium chloride solution
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7eb58348698e4ed88afc9d7d690ca4eb
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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