Thioacetamide → HCID 20605604, compound

HRID 481093Notes

Reaction equation

HRID 481093 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:21](=O)[CH:20](Br)[CH2:19][CH2:18][CH2:17][C:7]=2[N:8](C(OC(C)(C)C)=O)[CH:9]=1)=[O:4].[C:24]([NH2:27])(=[S:26])[CH3:25]>CO>[CH3:1][O:2][C:3]([C:5]1[C:6]2[C:21]3[N:27]=[C:24]([CH3:25])[S:26][C:20]=3[CH2:19][CH2:18][CH2:17][C:7]=2[NH:8][CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 20872400HCID 20872400, compound

Product 1

HCID 20605604HCID 20605604, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-Bromo-4-oxo-5,6,7,8-tetrahydro-4-H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester(880 mg, 2.27 mmol) and Thioacetamide(426 mg, 4.54 mmol) in MeOH(20 mL) is refluxed for 20 h and concentrated in vacuo. The residue is purified by flash chromatography on silica gel (50% EtOAc/Hex to 10% MeOH/CH2Cl2) to yield 382 mg of 2-Methyl-4,5,6,7-tetrahydro-3-thia-1,7-diaza-cyclopenta[e]azulene-9-carboxylic acid methyl ester as a yellow foam(64%). 1H NMR (CD3OD) 2.18 (quint, 2H), 2.61 (s, 3H), 2.70 (t, 2H) 2.78 (t, 2H), 3.73 (s, 3H), 7.29 (s, 1H)

Workup

  1. temperatureis refluxed for 20 h
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by flash chromatography on silica gel (50% EtOAc/Hex to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9d69a127375d44d5933c000b80f2a276
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

Loading…