Thiourea → HCID 86666220, compound

HRID 705942Notes

Reaction equation

HRID 705942 reaction equation
[OH:1]/[CH:2]=[C:3](/[CH2:8][N:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)\[C:4](OC)=O.[NH2:18][C:19]([NH2:21])=[S:20]>CO>[N:9]1([CH2:8][C:3]2[C:2](=[O:1])[NH:18][C:19](=[S:20])[NH:21][CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10]1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 67953507Methyl(2Z)-3-hydroxy-2-(1H-indol-1-ylmethyl)-2-propenoate

Product 1

HCID 86666220HCID 86666220, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl (2Z)-3-hydroxy-2-(1H-indol-1-ylmethyl)-2-propenoate (1.138 g, 4.92 mmol) in MeOH (20 mL) was added thiourea (1.0 g, 13.14 mmol) in one portion. The mixture was heated at 50° C. overnight. Purification via reverse phase flash chromatography then afforded the title compound (0.93 g, 3.47 mmol, 70.5% yield). LCMS: rt=2.28 min, [M+H+]=258

Workup

  1. customPurification via reverse phase flash chromatography

Sources & evidence

ORD record
ord-335f4cea5a11425b97d2898a125f8f93
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…