Dimethylamine → N,N-Dimethyl-3-(5-phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-benzamide

HRID 2075734Notes

Reaction equation

HRID 2075734 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][C:13]([S:17][C:18]4[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=4)[C:21](O)=[O:22])=[CH:14][CH:15]=3)[N:10]3[CH:27]=[N:28][N:29]=[C:9]3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH3:36][N:37](C=O)[CH3:38].CNC>C(Cl)Cl>[CH3:36][N:37]([CH3:38])[C:21](=[O:22])[C:20]1[CH:24]=[CH:25][CH:26]=[C:18]([S:17][C:13]2[CH:12]=[C:11]3[C:16]([C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8][C:9]4[N:10]3[CH:27]=[N:28][N:29]=4)=[CH:15][CH:14]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 529353193-(5-Phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-benzoic acid

Product 1

HCID 67090957N,N-Dimethyl-3-(5-phenyl-[1,2,4]triazolo[4,3-a]quinolin-8-ylsulfanyl)-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11a (219 mg, 0.67 mmol) in CH2Cl2 (30 mL) was added oxalyl chloride (0.07 mL, 0.80 mmol) and a drop of DMF. The mixture was then concentrated, and the residue was redissolved in CH2Cl2 and divided into 5 portions. To one portion, dimethylamine (2.0M, 0.3 mL, 0.54 mmol) was added, and the mixture was stirred at room temperature until no SM was observed by LCMS analysis. The reaction was concentrated and purified by preparative HPLC to give the desired product, 11b.

Workup

  1. concentrationThe mixture was then concentrated
  2. dissolutionthe residue was redissolved in CH2Cl2
  3. concentrationThe reaction was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-75f1cc375ec847c7bd6309106f4c88ec
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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