Triethylamine → HCID 60161550, compound

HRID 1843297Notes

Reaction equation

HRID 1843297 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.[C:22]1([CH3:31])[C:23]([N:28]=[C:29]=[O:30])=[CH:24][CH:25]=[CH:26][CH:27]=1>O1CCCC1>[CH3:31][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29](=[O:30])[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

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanateHCID 86704185HCID 86704185, compound

Product 1

HCID 60161550HCID 60161550, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 1-(prop-2-ynyl)-1,2,3,4-tetrahydroquinolin-7-ol (250 mg, 1.34 mM) and triethylamine (0.2 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, o-tolyl isocyanate (250 mg/ml, 2.01 mM) was added at once and then the reaction mixture was further stirred for 48 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 give 10a as solid. Yield: 300 mg, 70.13%.

Workup

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 48 hours under N2 atmosphere at RT
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. additionwas added
  5. distillationdistilled water (15 mL)
  6. extractionfollowed by the extraction with ether (3×15 mL)
  7. dry with materialThe ether layer was dried over sodium sulphate
  8. concentrationconcentrated under vacuum
  9. customto afford the crude product, which
  10. customwas finally chromatographed

Sources & evidence

ORD record
ord-5f5564e3b49f433d9d2f71aabfba12d7
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

Loading…