p-Toluenesulfonic acid → 1-{13-methyl-4-[1-(propan-2-yl)-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

HRID 1530664Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 12-(1-ethoxyethenyl)-13-methyl-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (160 mg, 0.440 mmol) and p-toluenesulfonic acid (7.5 mg, 0.044 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-{13-methyl-4-[1-(propan-2-yl)-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 (120 mg, 81% yield). LCMS (ESI) m/z: 352.2 [M+H+].

Workup

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

Sources & evidence

ORD record: ord-c8bc90becea249f59ce6c60659242772
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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