Dimethylformamide → HCID 69585794, compound

HRID 889896Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11](=[S:13])[NH2:12])[S:10][C:3]=12.CN(C=O)C.Cl[CH:20]([C:26]([CH3:28])=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[CH2:24]([O:23][C:21]([C:20]1[S:13][C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[N:12][C:26]=1[CH3:28])=[O:22])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

19.5 g (85.6 mmol) of 7-chloro-thieno[3,2-b]pyridine-2-carbothioic acid amide was added to 160 mL of a 1:1 DMF:THF solution mixture and cooled to 0° C. To this solution was slowly added 17.7 mL (128 mmol) of ethyl 2-chloroacetoacetate. After addition, the reaction was heated to 80° C. for sixteen hours. The reaction was cooled to room temperature and extracted with dichloromethane and water. The organic layer was separated and dried over magnesium sulfate, filtered, concentrated and purified by silica gel chromatography to afford 2-(7-Chloro-thieno[3,2-b]pyridin-2-yl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (15.6 g) in 54% yield. C14H11ClN2O2S2: APCI m/z 339.1/341.0 (pos.); 1H NMR (CDCl3): δ 8.68 (d, 1H , J=5.4 Hz), 8.24 (s, 1H), 7.51 (d, 1H, J=5.4 Hz), 4.36 (q, 2H, J=7.1 Hz), 2.77 (s, 3H), 1.38 (t, 3H, J=7.1 Hz) ppm.

Workup

additionAfter addition
temperatureThe reaction was cooled to room temperature
extractionextracted with dichloromethane and water
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-ae94746106f24abbab2665600e567b57
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995171B2

Reaction notes

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