p-Toluenesulfonic acid monohydrate → HCID 178508763, compound

HRID 2281581Notes

Reaction equation

HRID 2281581 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O1CCCCC1[O:19][CH2:20][CH2:21][N:22]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:31]([N:33]3[CH2:54][CH2:53][C:36]4([NH:40]/[C:39](=[N:41]/[C:42]([C:44]5[C:49]([NH2:50])=[N:48][C:47]([NH2:51])=[C:46]([Cl:52])[N:45]=5)=[O:43])/[NH:38][CH2:37]4)[CH2:35][CH2:34]3)=[O:32])[C:25]=2[CH:24]=[CH:23]1>CO>[OH:19][CH2:20][CH2:21][N:22]1[C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([C:31]([N:33]3[CH2:34][CH2:35][C:36]4([NH:40]/[C:39](=[N:41]/[C:42]([C:44]5[C:49]([NH2:50])=[N:48][C:47]([NH2:51])=[C:46]([Cl:52])[N:45]=5)=[O:43])/[NH:38][CH2:37]4)[CH2:53][CH2:54]3)=[O:32])[C:25]=2[CH:24]=[CH:23]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178508762HCID 178508762, compound

Product 1

HCID 178508763HCID 178508763, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Toluenesulfonic acid monohydrate (1.6 mg, 0.0084 mmol) is added to a stirred solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid [8-{1-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-1H-indole-4-carbonyl}-1,3,8-triaza-spiro[4.5]dec-(2E)-ylidene]-amide (Ex. 84) (50 mg, 0.084 mmol) in MeOH (3 ml) and the resulting solution is stirred at room temperature for 3 hrs, then heated at 50° C. for 16 hours. The solvent is removed in vacuo and the residue is dissolved in MeOH (3 ml) and loaded onto a 1 g PEAX cartridge which is eluted with MeOH (20 ml). The filtrate is concentrated in vacuo to afford the title compound; [M+H]+ 512/514

Workup

  1. temperatureheated at 50° C. for 16 hours
  2. customThe solvent is removed in vacuo
  3. dissolutionthe residue is dissolved in MeOH (3 ml)
  4. washis eluted with MeOH (20 ml)
  5. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-6e4cb77a54a04ac1b2eff8c604eb5a47
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

Loading…