p-Toluenesulfonic acid → 1-{4-[1-(2-hydroxyethyl)-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 1530652Notes

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][CH2:26][OH: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>[OH:27][CH2:26][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

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-{5-[12-(1-ethoxyethenyl)-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-4-yl]-1H-1,2,4-triazol-1-yl}ethan-1-ol (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 minute. The solid was filtered off, the filtrate was purified by reverse phase Combiflash eluting with a 0-40% gradient of CH3CN in 0.3% NH4HCO3 to give 1-{4-[1-(2-hydroxyethyl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2,4,10,12-pentaen-12-yl}ethan-1-one (120 mg, 81% yield). LCMS (ESI) m/z: 340.3 [M+H+].

Workup

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

Sources & evidence

ORD record: ord-a4199885bfb545e79251aa102b877950
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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