p-Toluenesulfonic acid → HCID 68313061, compound

HRID 1530726Notes

Reaction equation

HRID 1530726 reaction equation
C([O:3][C:4]([C:6]1[CH:19]=[C:18]2[C:9]([O:10][CH2:11][CH2:12][N:13]3[C:17]2=[N:16][C:15]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[N:23]=[C:22]([CH3:28])[N:21]=2)=[CH:14]3)=[CH:8][C:7]=1[O:29][CH3:30])=[CH2:5])C.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:30][O:29][C:7]1[CH:8]=[C:9]2[C:18](=[CH:19][C:6]=1[C:4](=[O:3])[CH3:5])[C:17]1[N:13]([CH:14]=[C:15]([C:20]3[N:24]([CH:25]([CH3:26])[CH3:27])[N:23]=[C:22]([CH3:28])[N:21]=3)[N:16]=1)[CH2:12][CH2:11][O:10]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68312958HCID 68312958, compound

Product 1

HCID 68313061HCID 68313061, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 13-(1-ethoxyethenyl)-12-methoxy-4-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaene (2.00 g) and 4-methylbenzenesulfonic acid (438 mg, 2.54 mmol) in acetone (20.0 mL) was stirred at 60° C. for 75 min. After removal of the solvent, the residue was purified by silica gel chromatography using 1-10% MeOH in DCM as eluant to afford the desired product (1.14 g, 80% yield for two steps). LCMS m/z [M+H]+ 382.3

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-6a8fc83a886d40409d51ddaca778dba8
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

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