2-Thiophenecarboxaldehyde, 5-chloro- → {4-[(5-Chloro-thiophen-2-ylmethyl)-amino]-2,6-dimethyl-phenyl}-carbamic acid propyl ester

HRID 1820149Notes

Reaction equation

[CH2:1]([O:4][C:5](=[O:16])[NH:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([NH2:14])=[CH:9][C:8]=1[CH3:15])[CH2:2][CH3:3].[Cl:17][C:18]1[S:22][C:21]([CH:23]=O)=[CH:20][CH:19]=1.C([BH3-])#N.[Na+].O.[Cl-].[Na+].O>CO>[CH2:1]([O:4][C:5](=[O:16])[NH:6][C:7]1[C:8]([CH3:15])=[CH:9][C:10]([NH:14][CH2:23][C:21]2[S:22][C:18]([Cl:17])=[CH:19][CH:20]=2)=[CH:11][C:12]=1[CH3:13])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 130 °C

Procedure

(4-Amino-2,6-dimethyl-phenyl)-carbamic acid propyl ester (84 mg) and 5-chloro-thiophene-2-carbaldehyde (48 uL) were dissolved in methanol (3 mL) and heated to 130° C. for 5 minutes in a sealed microwave process vial. Sodium cyanoborohydride (95 mg) was added and the reaction mixture was heated to 130° C. for 5 minutes in a sealed microwave process vial, followed by addition of water/brine (1:1, 3 mL). The product was extracted with ethyl acetate (3×3 mL) and the combined organic phases were washed with brine (5 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 66 mg (49% yield) of the title compound as an oil. LC-MS (m/z) 353 (MH+); tR=3.06, (UV, ELSD) 87%, 87%.

Workup

temperaturethe reaction mixture was heated to 130° C. for 5 minutes in a sealed microwave process vial
extractionThe product was extracted with ethyl acetate (3×3 mL)
washthe combined organic phases were washed with brine (5 mL)
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-efce2a94360740d0bc3b9cacfd4823b4
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601870B2

Reaction notes

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