2,4-Dimethoxybenzylamine → HCID 86731676, compound

HRID 1504784Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([CH3:11])[CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12.[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH2:17]>CN1CCCC1=O.C(OCC)(=O)C.P([O-])([O-])([O-])=O>[CH3:12][O:13][C:14]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:15]=1[CH2:16][NH:17][C:2]1[N:3]=[C:4]([CH3:11])[CH:5]=[C:6]2[CH:10]=[CH:9][S:8][C:7]=12

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 7-chloro-5-methyl-thieno[2,3-c]-pyridine (100 mg, 0.544 mmol) and 2,4-dimethoxybenzylamine (0.245 mL, 1.63 mmol) in 1-methyl-2-pyrrolidinone (2 mL) was heated to 180° C. in an oil bath for 19 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (30 mL) and aqueous phosphate buffer (1.0 M, pH 7, 20 mL). The separated organics were sequentially washed with water (10 mL), aqueous phosphate buffer (1.0 M, pH 7, 10 mL), water (10 mL), and brine (10 mL). The organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (5-25% ethyl acetate/hexanes, linear gradient) to give N-(2,4-dimethoxybenzyl)-5-methylthieno[2,3-c]pyridin-7-amine. MS ESI calc'd. for C17H19N2O2S [M+H]+ 315. found 315.

Workup

temperatureAfter cooling to room temperature
washThe separated organics were sequentially washed with water (10 mL), aqueous phosphate buffer (1.0 M, pH 7, 10 mL), water (10 mL), and brine (10 mL)
dry with materialThe organics were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on silica gel (5-25% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record: ord-fa494449dfce43cfbaf5e33c52b9ddb6
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216173B2

Reaction notes

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