Hydrochloric Acid → HCID 131730223, compound

HRID 388524Notes

Reaction equation

HRID 388524 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)=[O:17])[CH:10]=2)[C:5]([F:23])=[CH:4][C:3]=1[NH:24][C:25]([CH2:27][C:28]1([CH2:31][C:32]([NH:34][C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)=[O:33])[CH2:30][CH2:29]1)=[O:26].[ClH:42].O>CC(C)=O>[ClH:42].[F:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([N:18]3[CH2:19][CH:20]([OH:22])[CH2:21]3)=[O:17])[CH:10]=2)[C:5]([F:23])=[CH:4][C:3]=1[NH:24][C:25]([CH2:27][C:28]1([CH2:31][C:32]([NH:34][C:35]2[CH:36]=[CH:37][C:38]([F:41])=[CH:39][CH:40]=2)=[O:33])[CH2:30][CH2:29]1)=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 131730221HCID 131730221, compound

Product 1

HCID 131730223HCID 131730223, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
50 °C

Procedure

N-{2,5-Difluoro-4-[(2-{[(3-hydroxyazetidin-1-yl)carbonyl]amino}pyridin-4-yl)oxy]phenyl}-N′-(4-fluorophenyl)cyclopropane-1,1-dicarboxyamide (32.5 mg) was suspended in acetone (0.325 ml). 5N hydrochloric acid (0.012 ml) was added at room temperature. After adding water (0.151 ml), the mixture was heated and stirred at 50° C. for 5 minutes to form a solution. The solution was stirred at room temperature for 30 minutes, acetone (0.325 ml) was added, and stirring was continued for 26 hours. The precipitate was collected by filtration and washed with acetone (0.163 ml, twice). It was then dried under aeration at room temperature for 1 hour and then dried with warm air at 60° C. for 12 hours to give the title compound (27.6 mg, 80%) as white crystals.

Workup

  1. temperaturethe mixture was heated
  2. customto form a solution
  3. stirringThe solution was stirred at room temperature for 30 minutes
  4. stirringstirring
  5. waitwas continued for 26 hours
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with acetone (0.163 ml
  8. customIt was then dried under aeration at room temperature for 1 hour
  9. customdried
  10. temperaturewith warm air at 60° C. for 12 hours

Sources & evidence

ORD record
ord-c6b60bc8106d462c900d1f18bb2c7e50
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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