Benzenesulfonic Acid → HCID 131730227, compound

HRID 388528Notes

Reaction equation

HRID 388528 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].[C:42]1([S:48]([OH:51])(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C(O)C>[C:42]1([S:48]([OH:51])(=[O:50])=[O:49])[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=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 7371Benzenesulfonic AcidHCID 131730221HCID 131730221, compound

Product 1

HCID 131730227HCID 131730227, compoundYield 75.3%

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 (31.6 mg) was suspended in ethanol (0.316 ml). After adding benzenesulfonic acid (10.2 mg) at room temperature to form a solution, it was stirred at room temperature for 17 hours and 50 minutes. Ethanol (0.5 ml) was added, and then 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 (30.4 mg, 74%) as white crystals.

Workup

  1. customto form a solution, it
  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-163f86cbaeb64f7dac7c88184bf890d5
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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