Diethylamine → HCID 131736278, compound

HRID 1053512Notes

Reaction equation

HRID 1053512 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[C:6]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)(=[O:9])[C:7]#[CH:8]>C1COCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[CH:8]=[CH:7][C:6]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 10560973HCID 10560973, compound

Product 1

HCID 131736278HCID 131736278, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylamine (66 mg, 0.89 mmol) and compound 1 (200 mg, 0.89 mmol) were dissolved in dry THF (20 mL), and the solution was stirred at RT for 15 min. The solvent was removed under reduced pressure to give the crude product which was then purified by column chromatography using ethyl acetate:hexane (7:3) to give compound 2 (237 mg, 89%). 1H NMR (400 MHz, CDCl3) δ 1.24 (t, J=7.0 Hz, 6H), 3.28 (br. s, 4H), 4.79 (d, J=13.0 Hz, 1H), 7.20 (d, J=8.6 Hz, 2H), 7.36 (t, J=7.4 Hz, 1H), 7.44 (t, J=7.8 Hz, 2H), 7.62 (m, 4H), 7.63 (d, J=13.0 Hz, 1H). HRMS ESI (m/z): Calculated for C19H21NO2 ([M+H]+): 296.1572. found: 296.1647.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give the crude product which
  3. customwas then purified by column chromatography

Sources & evidence

ORD record
ord-11cd6f84b11b46ab9aad831e485ab9d7
Source dataset
uspto-grants-2016_07
Patent number
US09393306B2

Reaction notes

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