Triethylamine → HCID 60161669, compound

HRID 1843299Notes

Reaction equation

[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].C(N(CC)CC)C.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]=[C:30]=[O:31]>O1CCCC1>[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][C:30](=[O:31])[O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][CH2:5][N:4]2[CH2:1][C:2]#[CH:3])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A mixture of 1-(prop-2-ynyl)-1,2,3,4-tetrahydroquinolin-7-ol (400 mg, 2.14 mM) and triethylamine (0.6 mL) in dry tetrahydrofuran (THF, 5 mL) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, 2-bromophenyl isocyanate (396 mg/ml, 3.21 mM) was added at once and then the reaction mixture was further stirred for 36 hours under N2 atmosphere at RT. The reaction mixture was concentrated under vacuum and then was added distilled water (15 mL) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chlorophorm-hexane (1:19) to afford 10c as solid. Yield: 540 mg, 65.61%.

Workup

additionwas added at once and then the reaction mixture
stirringwas further stirred for 36 hours under N2 atmosphere at RT
concentrationThe reaction mixture was concentrated under vacuum
additionwas added
distillationdistilled water (15 mL)
extractionfollowed by the extraction with ether (3×15 mL)
dry with materialThe ether layer was dried over sodium sulphate
concentrationconcentrated under vacuum
customto afford the crude product, which
customwas finally chromatographed

Sources & evidence

ORD record: ord-2d18c45bd92e4f658e2927cb55c43154
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946261B2

Reaction notes

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