p-Toluenesulfonic acid → 1-{12-Methyl-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-pentaen-13-yl}ethan-1-one

HRID 1530706Notes

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[CH3:29])=[CH2:5])C.CC1C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[CH3:29][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

Conditions

Temperature: 60 °C

Procedure

A mixture of 13-(1-ethoxyethenyl)-12-methyl-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 (2.0 g) and 4-methylbenzenesulfonic acid (438 mg, 2.54 mmol) in acetone (20.0 mL) was stirred at 60° C. for 75 min. The solvent was removed to give the desired compound (2.20 g, over 100% yield) as yellow oil, which was used directly in the next step without further purification. LCMS m/z [M+H]+ 366.2

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-b963c1dcb76043999d0122258b8bb478
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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