Dimethylformamide → HCID 69673423, compound

HRID 2041879Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

550 mg of 2-vinyl-4-phenyl-3-butynylamine, 500 mg of 4-chloroquinazoline, and 636 μl of triethylamine were added to 15 ml of DMF, and the obtained mixture was then stirred at 80° C. for 5 hours. Thereafter, the reaction solution was cooled, and 20 ml of water was then added thereto, followed by extraction with 50 ml of ethyl acetate twice. The organic layer was washed with 50 ml of a saturated brine twice, and it was then dried over sodium sulfate. The sodium sulfate was filtrated, and the organic layer was then concentrated. The residue was purified using an automated flash chromatography instrument (manufactured by Biotage AB; Isolera™), so as to obtain 750 mg of a product of interest.

Workup

temperatureThereafter, the reaction solution was cooled
extractionfollowed by extraction with 50 ml of ethyl acetate twice
washThe organic layer was washed with 50 ml of a saturated brine twice
dry with materialit was then dried over sodium sulfate
filtrationThe sodium sulfate was filtrated
concentrationthe organic layer was then concentrated
customThe residue was purified

Sources & evidence

ORD record: ord-4ecf697ab20141078d39b69ea1b7d271
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586505B2

Reaction notes

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