Diisopropylethylamine → HCID 66919692, compound

HRID 523876Notes

Reaction equation

HRID 523876 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][S:8][C:9]2[N:14]=[C:13]([C:15](Cl)=[O:16])[CH:12]=[CH:11][C:10]=2[C:18]#[N:19])=[CH:5][CH:4]=1.[CH:22]([N:25](CC)C(C)C)(C)C>CN(C)C=O>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][S:8][C:9]2[N:14]=[C:13]([C:15]([NH:25][CH3:22])=[O:16])[CH:12]=[CH:11][C:10]=2[C:18]#[N:19])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86650826HCID 86650826, compound

Product 1

HCID 66919692HCID 66919692, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-(4-chlorobenzylthio)-5-cyanopicolinoyl chloride hydrochloride 81 (60 mg, 0.17 mmol) and N,N-diisopropylethylamine (89 ul, 0.51 mmol) in dimethylformamide (2 ml) was stirred for 6 hrs at room temperature. After removal of the solvent, the residue was triturated with ether and the resulting solid was collected by filtration to afford 40 mg (74%) of the desired product 84. 1H NMR (600 MHz, DMSO-d6) δ 8.79 (d, 1H, J=4.8 Hz), 8.37 (d, 1H, J=7.8 Hz), 7.84 (d, 1H, J=8.4 Hz), 7.49 (d, 2H, J=9 Hz), 7.38 (d, 2H, 9 Hz), 4.76 (s, 2H), 2.89 (d, 3H, J=4.8 Hz). MS: m/z Calcd 317.8 Found MH+ 318.0

Workup

  1. customAfter removal of the solvent
  2. customthe residue was triturated with ether
  3. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-c318785ba7db4c6592eed609d2a9e2ff
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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