Hydrochloric Acid → HCID 178493581, compound

HRID 1297618Notes

Reaction equation

HRID 1297618 reaction equation
CO[C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11](/[CH:17]=[C:18]1/[C:19](=[O:33])[N:20]=[C:21]([NH:23][C@@H:24]3[CH2:26][C@H:25]3[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[S:22]/1)=[CH:10][CH:9]=2)=[O:4].C[NH:35][CH2:36][CH2:37][NH:38][CH3:39].Cl.[CH:41](Cl)(Cl)Cl>>[CH3:41][N:38]([CH3:39])[CH2:37][CH2:36][NH:35][C:3]([C:5]1[CH:6]=[N:7][C:8]2[C:13]([C:14]=1[O:15][CH3:16])=[CH:12][C:11](/[CH:17]=[C:18]1/[C:19](=[O:33])[N:20]=[C:21]([NH:23][C@@H:24]3[CH2:26][C@H:25]3[C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[S:22]/1)=[CH:10][CH:9]=2)=[O:4]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 8070N,N'-DimethylethylenediamineHCID 178498733HCID 178498733, compound

Product 1

HCID 178493581HCID 178493581, compound

Conditions

Temperature
120 °C

Procedure

To the suspension of 4-methoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carboxylic acid methyl ester (example 1) (50 mg, 0.11 mmol) in chloroform (5 mL) was added dimethylethylenediamine (0.048 mL, 0.44 mmol). The mixture was stirring at 120° C. for 3 h. After cooling, the solid was collected by filtration and washed with methylenechloride. The solid was dissolved in acetonitrile and 1N hydrochloride acid (0.22 mL, 0.22 mmol) was added. The resulting solution was lyophilized to give 4-methoxy-6-[4-oxo-2-((1R,2S)-2-phenyl-cyclopropylamino)-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carboxylic acid (2-dimethylamino-ethyl)-amide; hydrochloride. LC-MS m/e 516 (MH+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid was collected by filtration
  3. washwashed with methylenechloride
  4. dissolutionThe solid was dissolved in acetonitrile

Sources & evidence

ORD record
ord-3b84feab971841fd8c21153319102662
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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