Caffeic Acid → HCID 178464065, compound

HRID 1500394Notes

Reaction equation

[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[C:30]([OH:42])(=[O:41])/[CH:31]=[CH:32]/[C:33]1[CH:40]=[CH:39][C:37]([OH:38])=[C:35]([OH:36])[CH:34]=1>CO>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][NH:8][C:9]([C:11]1[C:12]([CH3:29])=[C:13](/[CH:17]=[C:18]2/[C:19]3[CH:20]=[C:21]([F:28])[CH:22]=[CH:23][C:24]=3[NH:25][C:26]/2=[O:27])[NH:14][C:15]=1[CH3:16])=[O:10])[CH2:4][CH3:5].[C:30]([O-:42])(=[O:41])/[CH:31]=[CH:32]/[C:33]1[CH:40]=[CH:39][C:37]([OH:38])=[C:35]([OH:36])[CH:34]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Sunitinib (1.0 g) was suspended in methanol (152 mL), followed by addition of caffeic acid (0.45 g) at 25-35° C. over a period of 15 minutes. After the stipulated time period, methanol was completely distilled off under vacuum below 45° C. The residue was treated with acetonitrile (38 mL) and refluxed. The reaction mass was maintained at reflux temperature for 60 minutes. The reaction mass was cooled to 25-35° C. for crystallization. The solid obtained was filtered, washed with acetonitrile, suck dried and dried under vacuum at 60° C. over 4-5 hr period to obtain sunitinib caffeate. (1.3 g; yield:89%)

Workup

distillationAfter the stipulated time period, methanol was completely distilled off under vacuum below 45° C
additionThe residue was treated with acetonitrile (38 mL)
temperaturerefluxed
temperatureThe reaction mass was maintained
temperatureat reflux temperature for 60 minutes
customThe solid obtained
filtrationwas filtered
washwashed with acetonitrile, suck
customdried
customdried under vacuum at 60° C. over 4-5 hr period

Sources & evidence

ORD record: ord-887ac5850ca64a5b9f347ca958eab3ab
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206163B2

Reaction notes

Loading…