p-Toluenesulfonic acid monohydrate → Acetamide,n-[2-[4-[[3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl]amino]-5h-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl]-2-(methylsulfonyl)-,mono(4-methylbenzenesulfonate)

HRID 1926136Notes

Reaction equation

HRID 1926136 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][NH:31][C:32](=[O:38])[CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1.O.[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:43][CH:42]=1>C(OCC)(=O)C>[CH3:40][C:41]1[CH:42]=[CH:43][C:44]([S:47]([OH:50])(=[O:49])=[O:48])=[CH:45][CH:46]=1.[Cl:1][C:2]1[CH:3]=[C:4]([NH:19][C:20]2[C:21]3[N:28]([CH2:29][CH2:30][NH:31][C:32](=[O:38])[CH2:33][S:34]([CH3:37])(=[O:36])=[O:35])[CH:27]=[CH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[CH:10]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 57597166N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-2-(methylsulfonyl)acetamide

Product 1

HCID 76852991Acetamide,n-[2-[4-[[3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl]amino]-5h-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl]-2-(methylsulfonyl)-,mono(4-methylbenzenesulfonate)Yield 76.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{2-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]ethyl}-2-(methylsulfonyl)acetamide (150 mg) in ethyl acetate (10 mL) was added 4-methylbenzenesulfonic acid monohydrate (55.4 mg) at room temperature. The mixture was stirred at room temperature for 20 hrs, and the solvent was evaporated under reduced pressure. The precipitated crystals were collected by filtration and washed with ethyl acetate and diisopropyl ether to give the title compound (150.3 mg) as colorless crystals.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-6e899469724a483ead3b7a3c9e49a8bf
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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