Dimethylformamide → HCID 17756177, compound

HRID 2382554Notes

Reaction equation

CS([C:4]1[O:5][C:6]2[C:11]([C:12](=[O:15])[C:13]=1[CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=2)=O.[NH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][CH2:27][OH:28])=[CH:20][CH:19]=1.CN(C=O)C>C(#N)C>[OH:28][CH2:27][CH2:26][CH2:25][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([CH2:17][NH:16][C:4]2[O:5][C:6]3[C:11]([C:12](=[O:15])[C:13]=2[CH3:14])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-methanesulfinyl-3-methyl-chromen-4-one (0.35 g, 1.78 mmol) in acetonitrile (37 mL), 4-(4-aminomethyl-phenyl)-butan-1-ol (0.47 g, 2.13 mmol) and DMF (18 mL) were added. The reaction stirred in a 50° C. oil bath overnight under N2 atmosphere. The next day, the reaction mixture was cooled to room temperature and concentrated to yield an oil. Purification of the oil by flash column chromatography (100% ethyl acetate) afforded the desired product as a white solid (120 mg, 20% yield). 1H NMR (600 MHz, CDCl3): δ 8.20 (d, 1H, J=7.9 Hz), 7.53 (t, 1H, J=7.8 Hz), 7.35 (t, 1H, J=7.6 Hz), 7.31 (d, 1H, J=8.4 Hz), 7.29 (d, 2H, J=7.9 Hz), 7.21 (d, 2H, J=7.9 Hz), 4.82 (bt, 1H, J=5.9 Hz), 4.66 (d, 2H, J=5.6 Hz), 3.68 (m, 2H), 2.66 (t, 2H, J=7.5 Hz), 1.97 (s, 3H), 1.70 (m, 2H), 1.61 (m, 2H), 1.24 (bt, 1H, J=5.3 Hz); 13C NMR (150 MHz, CDCl3): δ 174.0, 160.3, 152.2, 141.4, 135.5, 130.7, 128.2, 126.9, 125.0, 123.8, 122.3, 115.8, 92.7, 61.5, 44.6, 34.8, 31.8, 27.2, 7.3.

Workup

temperatureThe next day, the reaction mixture was cooled to room temperature
concentrationconcentrated
customto yield an oil
customPurification of the oil by flash column chromatography (100% ethyl acetate)

Sources & evidence

ORD record: ord-b23cf4a5dbd447ebadb398406bb39745
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263042B2

Reaction notes

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