Triethylamine → HCID 59700593, compound

HRID 901962Notes

Reaction equation

HRID 901962 reaction equation
S(Cl)(Cl)=[O:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]([CH2:17][C:18]2(C(O)=O)[NH:22]C=[CH:20][S:19]2)[CH3:16])(=[O:14])=[O:13])=[CH:8][CH:7]=1.[CH2:26]([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])[CH3:27].N1[C:42]2[C:37](=CC=CC=2)[CH2:36][CH2:35][CH2:34]1>ClCCl.CCOC(C)=O>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([S:12]([N:15]([CH2:17][C:18]2[S:19][CH:20]=[C:27]([C:26]([N:28]3[C:31]4[C:35](=[CH:36][CH:37]=[CH:42][CH:32]=4)[CH2:34][CH2:30][CH2:29]3)=[O:2])[N:22]=2)[CH3:16])(=[O:13])=[O:14])=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 694601,2,3,4-TetrahydroquinolineHCID 69207421HCID 69207421, compound

Product 1

HCID 59700593HCID 59700593, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Thionyl chloride (2.0 ml) was added to a solution of 2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole carboxylic acid (460 mg, 1.2 mmol) in dichloromethane (20 ml) and the solution heated at reflux for 2 h. The mixture was cooled to room temperature, reduced in vacuo and azeotroped with toluene to yield a white solid. This was dissolved in dichloromethane (20 ml) and to it were added triethylamine (0.34 ml, 250 mg, 2.4 mmol) and 1,2,3,4-tetrahydroquinoline (0.18 ml, 190 mg, 1.4 mmol). After stirring for 1 h the mixture was reduced in vacuo. Chromatography (50% EtOAc/50% hexanes) afforded 1-(2-(N-(4-bromobenzenesulphonyl)-N-methylaminomethyl)thiazole-4-carbonyl)-1,2,3,4-tetrahydroquinoline (580 mg, 97%) as a white solid.

Workup

  1. temperaturethe solution heated
  2. temperatureat reflux for 2 h
  3. customazeotroped with toluene
  4. customto yield a white solid

Sources & evidence

ORD record
ord-1a5c6827b2254b14893916eaecbb1361
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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