Dimethylamine → HCID 44594045, compound

HRID 1400173Notes

Reaction equation

HRID 1400173 reaction equation
[CH:1]([C:3]1[S:4][C:5]2[NH:6][C:7](=[O:16])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[N:15]=1)=[CH2:2].[CH3:17][NH:18][CH3:19]>C(Cl)Cl.CO>[CH3:17][N:18]([CH3:19])[CH2:2][CH2:1][C:3]1[S:4][C:5]2[NH:6][C:7](=[O:16])[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14]=2[N:15]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 58016050HCID 58016050, compound

Product 1

HCID 44594045HCID 44594045, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-vinyl-4H-1,3-thiazolo[5,4-c]isoquinolin-5-one (0.05 g, 0.22 mmol) and CH2Cl2/methanol (6 ml; 1/1) was added dimethylamine (0.33 ml of 2M solution in THF, 0.66 mmol). After stirring at 65° C. for 48 hours, the reaction mixture was concentrated under reduced pressure and purified by flash-chromatography (CH2Cl2/methanol, 90/10). Recrystallization from methanol/diethyl ether yielded 0.038 g (a 63% yield) of the title compound as a white solid. m.p. 236-240° C. (dec.); 1H NMR (400 MHz, DMSO) δ 2.85 (s, 6H, (CH2)2N(CH3)2), 3.52-3.56 (m, 4H, (CH2)2N(CH3)2), 7.56-7.59 (m, 1H, Ar), 7.84-7.87 (m, 1H, Ar), 8.19-8.26 (m, 2H, Ar), 12.37 (bs, NH); 13C NMR (100.6 MHz, DMSO) δ 29.71, 44.26, 56.79, 124.03, 125.74, 128.69, 129.79, 133.45, 134.44, 135.15, 158.51, 162.72.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. custompurified by flash-chromatography (CH2Cl2/methanol, 90/10)
  3. customRecrystallization from methanol/diethyl ether

Sources & evidence

ORD record
ord-6d09c791a99c45769a8ed0ec7344d52e
Source dataset
uspto-grants-2014_12
Patent number
US08906935B2

Reaction notes

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