Triethylamine → HCID 58610091, compound

HRID 1442602Notes

Reaction equation

[C:1]([NH:9][CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24](OC)(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[SH:27].C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[C:1]([NH:9][CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[S:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[C:24](=[O:32])[N:23]=2)[CH:17]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 145 °C

Procedure

A mixture of methyl 2-(benzoylamino)-3-(3-cyanophenyl)propionate (201 mg, 0.652 mmol), methyl thiosalicylate (165 mg, 0.981 mmol), triethylamine (0.18 mL, 1.3 mmol) and xylene (0.65 ml) was stirred at 145° C. for 15 hours under a nitrogen flow. The reaction mixture was applied to silica gel column chromatography (gradient elution with hexane-ethyl acetate from 67:33 to 50:50). The eluate was crystallized from ethyl acetate-diisopropyl ether to give the title compound (49.7 mg, 17%).

Workup

washThe reaction mixture was applied to silica gel column chromatography (gradient elution with hexane-ethyl acetate from 67:33 to 50:50)
customThe eluate was crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-9cc28bfc19e7449898dd0c0906adb279
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659267B2

Reaction notes

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