Ethyl 2-chloroacetoacetate → HCID 68699956, compound

HRID 644045Notes

Reaction equation

[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19](=[S:21])[NH2:20])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH:23]([C:29](=O)[CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>CCO>[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[O:17][CH3:18])[C:10]([C:19]3[S:21][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:29]([CH3:30])[N:20]=3)=[CH:9]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide (604 mg, 2.00 mmol) in EtOH (5.0 ml) was added ethyl 2-chloro-3-oxobutanoate (0.332 ml, 2.40 mmol). The mixture was refluxed for 1 h. After cooling to 0° C., the precipitate was collected by filtration to afford 1-cyclohexylmethyl-3-(5-ethoxycarbonyl-4-methylthiazol-2-yl)-7-methoxy-1H-indole (505 mg, 1.22 mmol).

Workup

temperatureThe mixture was refluxed for 1 h
filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record: ord-f48099c6145a42f2928cc2f92f307c52
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700634B2

Reaction notes

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