Triethylamine → HCID 16375955, compound

HRID 2175691Notes

Reaction equation

HRID 2175691 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH2:3][C:2]1=[O:11].C(N(CC)CC)C.[CH3:19][O:20][C:21]1[CH:22]=[C:23](/[CH:29]=[CH:30]/[C:31](Cl)=[O:32])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>C1COCC1>[CH3:19][O:20][C:21]1[CH:22]=[C:23](/[CH:29]=[CH:30]/[C:31]([N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:1][C:2](=[O:11])[CH2:3]2)=[O:32])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1859492(1H)-Quinoxalinone, 3,4-dihydro-HCID 11806394(2E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chloride

Product 1

HCID 16375955HCID 16375955, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3,4-dihydroquinoxalin-2(1H)-one (142 mg, 0.96 mmol) and triethylamine (0.16 mL, 1.14 mmol) in anhydrous THF (15 mL) at 0° C. was added a solution of (E)-3-(3,4-dimethoxyphenyl)acryloyl chloride in THF (2 mL) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction was quenched by addition of 1N hydrochloric acid, and extracted with DCM. The combined organic phases were washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford the crude product which was purified by flash chromatography (hexane-EtOAc, 25:10) to give (E)-4-(3-(3,4-dimethoxyphenyl)acryloyl)-3,4-dihydroquinoxalin-2(1H)-one (160 mg, 47%). 1H-NMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 3.90 (s, 3H), 4.63 (br s, 2H), 6.71 (d, J=15.2 Hz, 1H), 6.85 (d, J=8.4 Hz, 1H), 6.94 (d, J=2.0 Hz, 1H), 7.02 (dd, J=7.6, 1.2 Hz, 1H), 7.07-7.13 (m, 2H), 7.22 (dd, J=7.6, 1.2 Hz, 1H), 7.28 (br d, J=8.0 Hz, 1H), 7.76 (d, J=15.6 Hz, 1H), 8.89 (s, 1H); LC-MS (ES-API); rt 8.14 min; m/z calculated for C19H18N2O4[M+H]+ 339.1, found 339.0.

Workup

  1. customThe reaction was quenched by addition of 1N hydrochloric acid
  2. extractionextracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product which
  7. customwas purified by flash chromatography (hexane-EtOAc, 25:10)

Sources & evidence

ORD record
ord-ebc9d916942848fbab2bdcd8dc46b58e
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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