p-Toluenesulfonic acid monohydrate → HCID 178424418, compound

HRID 1620487Notes

Reaction equation

HRID 1620487 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:8][CH2:7]1.O.[S:37]([C:41]1[CH:47]=[CH:46][C:44](C)=[CH:43][CH:42]=1)([OH:40])(=[O:39])=[O:38]>C(OCC)(=O)C>[C:3]1([CH3:2])[C:4]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:26][CH:27]=[CH:28][CH:29]=1.[C:47]1([CH3:2])[C:41]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:42][CH:43]=[CH:44][CH:46]=1.[F:35][C:2]([F:1])([F:34])[C:3]1[CH:29]=[C:28]([C:30]([F:32])([F:33])[F:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:13]2/[C:14]([NH:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][OH:25])=[N:15][C:16](=[O:18])[S:17]/2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178518154HCID 178518154, compound

Product 1

HCID 178424418HCID 178424418, compoundYield 185.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (5Z)-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-4-{[2-(2-hydroxyethoxy)ethyl]amino}-1,3-thiazol-2(5H)-one (4.3 g) in ethyl acetate (40 ml) was added tosylic acid monohydrate (3.11 g), and the mixture was stirred at room temperature for 2 hr. The precipitate was collected by filtration, washed with ethyl acetate, and recrystallized from 2-butanone/heptane to give the title compound (4.4 g).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate
  3. customrecrystallized from 2-butanone/heptane

Sources & evidence

ORD record
ord-6461c10a029e42a48254c6c4a9fa5d65
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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