p-Toluenesulfonic acid monohydrate → HCID 136335096, compound

HRID 226480Notes

Reaction equation

HRID 226480 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[N:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([NH:24][OH:25])=[O:23])=[N:18][CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[CH3:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:30][CH:29]=1>C(O)C>[CH3:27][C:28]1[CH:29]=[CH:30][C:31]([S:34]([OH:37])(=[O:36])=[O:35])=[CH:32][CH:33]=1.[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[N:15]=[CH:16][C:17](/[CH:20]=[CH:21]/[C:22]([NH:24][OH:25])=[O:23])=[N:18][CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 136335097HCID 136335097, compound

Product 1

HCID 136335096HCID 136335096, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide (300 mg) in 95% ethanol (3 mL) was added 4-methylbenzenesulfonic acid hydrate (168 mg) at ambient temperature. After stirring at the same temperature for one hour, additional 95% ethanol(1.5 mL) was added to the mixture. The precipitate was collected after two hours to afford (2E)-3-(5-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-2-pyrazinyl)-N-hydroxyacrylamide 4-methylbenzenesulfonate (253 mg) as a pale brown solid.

Workup

  1. customThe precipitate was collected after two hours

Sources & evidence

ORD record
ord-18bd7bc1ba0f47bd81d31a959cc3d82d
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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