p-Toluenesulfonic acid → HCID 68312923, compound

HRID 1530677Notes

Reaction equation

HRID 1530677 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:17](=[CH:18][CH:19]=1)[C:16]1[N:12]([CH:13]=[C:14]([C:20]3[N:24]([CH2:25][CH:26]([O:28][CH3:29])[CH3:27])[N:23]=[CH:22][N:21]=3)[N:15]=1)[CH2:11][CH2:10][O:9]2)=[CH2:5])C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:29][O:28][CH:26]([CH3:27])[CH2:25][N:24]1[C:20]([C:14]2[N:15]=[C:16]3[N:12]([CH:13]=2)[CH2:11][CH2:10][O:9][C:8]2[C:17]3=[CH:18][CH:19]=[C:6]([C:4](=[O:3])[CH3:5])[CH:7]=2)=[N:21][CH:22]=[N:23]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68313110HCID 68313110, compound

Product 1

HCID 68312923HCID 68312923, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 12-(1-ethoxyethenyl)-4-[1-(2-methoxypropyl)-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 (190 mg, 0.480 mmol) and p-toluenesulfonic acid (11 mg, 0.060 mmol) in acetone (10 mL) was stirred at 60° C. for 75 min. The solid was filtered off and the filtrate was concentrated. The residue was purified by reverse phase Combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to afford 1-{4-[1-(2-methoxypropyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaen-12-yl}ethan-1-one (160 mg, 91% yield). LCMS (ESI) m/z: 368.1 [M+H+]

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by reverse phase Combiflash
  4. washeluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3

Sources & evidence

ORD record
ord-a9464f4c2dae4b8ba6127f98be2c7730
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…