p-Toluenesulfonic acid monohydrate → HCID 58158152, compound

HRID 1916277Notes

Reaction equation

HRID 1916277 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[S:28][CH:29]=2)[N:3]=1.O.[C:38]1(C)[CH:43]=CC(S(O)(=O)=O)=C[CH:39]=1>CC(C)=O>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[S:28][CH:29]=[C:25]([CH2:24][S:23][C:4]3[C:5]([C:21]#[N:22])=[C:6]([C:11]4[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:15][CH:16]=4)[C:7]4[C:8](=[O:9])[NH:10][C:38]([CH3:43])([CH3:39])[NH:1][C:2]=4[N:3]=3)[N:26]=2)=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 58158129HCID 58158129, compound

Product 1

HCID 58158152HCID 58158152, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

50 mg (0.093 mmol) of the compound from Example 22A were initially charged in 2 ml of acetone, a spatula tip of 4-toluenesulfonic acid monohydrate was added and the mixture was stirred at reflux for 1 h. After cooling, the reaction solution was concentrated and the residue was purified directly by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA).

Workup

  1. temperatureat reflux for 1 h
  2. temperatureAfter cooling
  3. concentrationthe reaction solution was concentrated
  4. customthe residue was purified directly by preparative HPLC (Chromasil, water/acetonitrile+0.1% TFA)

Sources & evidence

ORD record
ord-77e518ce0c8a47358ab6daf405ffb711
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

Loading…