p-Toluenesulfonic acid monohydrate → HCID 131730228, compound

HRID 388529Notes

Reaction equation

HRID 388529 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].O.[C:43]1([CH3:53])[CH:48]=[CH:47][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:45][CH:44]=1>C(O)C>[CH3:53][C:43]1[CH:44]=[CH:45][C:46]([S:49]([OH:52])(=[O:51])=[O:50])=[CH:47][CH:48]=1.[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

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 131730221HCID 131730221, compound

Product 1

HCID 131730228HCID 131730228, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

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 (34.2 mg) was suspended in ethanol (0.342 ml). p-Toluenesulfonic acid monohydrate (13.2 mg) was added at room temperature to form a solution, which was then stirred at room temperature for 90 hours and 25 minutes. Ethanol (1 ml) was added, and the precipitate was collected by filtration and washed with tert-butyl methyl ether (1 ml, three times). It was then dried under aeration at room temperature for 1 hour to give the title compound (33.0 mg, 73%) as white crystals.

Workup

  1. customto form a solution, which
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with tert-butyl methyl ether (1 ml, three times)
  4. customIt was then dried under aeration at room temperature for 1 hour

Sources & evidence

ORD record
ord-f7976b88bcee4812b3902ace5fe5dc25
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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