Triethylamine → HCID 60161673, compound

HRID 1843300Notes

Reaction equation

HRID 1843300 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.[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1[N:32]=[C:33]=[O:34])([CH3:24])[CH3:23]>O1CCCC1>[CH:22]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:26]=1[NH:32][C:33](=[O:34])[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)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45246912-Isopropyl-6-methylphenyl isocyanateHCID 86704185HCID 86704185, compound

Product 1

HCID 60161673HCID 60161673, 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 (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-isopropyl-6-methylphenyl isocyanate (558 mg/ml, 3.21 mM) was added at once and then the reaction mixture was further stirred for 30 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 chloroform-hexane (1:19) to afford 10d as solid. Yield: 520 mg, 67.16%.

Workup

  1. additionwas added at once and then the reaction mixture
  2. stirringwas further stirred for 30 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-d53f68ff0a8846509ed7d2776b068bf7
Source dataset
uspto-grants-2015_02
Patent number
US08946261B2

Reaction notes

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