Triethylamine → HCID 67087718, compound

HRID 2175686Notes

Reaction equation

HRID 2175686 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:11]=[CH:12]/[C:13]([OH:15])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[O:16]1[CH2:21][CH2:20][NH:19][C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]1=2.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl.O>[O:16]1[CH2:21][CH2:20][N:19]([C:13](=[O:15])/[CH:12]=[CH:11]/[C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]1=2

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 5850963,4-Dihydro-2H-1,4-benzoxazineHCID 717531(E)-3,4-Dimethoxycinnamic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 67087718HCID 67087718, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-(3,4-dimethoxyphenyl)acrylic acid (0.46 g, 2.22 mmol) and 3,4-dihydro-2H-benzo[b][1,4]oxazine (0.20 g, 1.48 mmol) in DCM (15 mL) was added EDC.HCl (0.71 g, 3.70 mmol), HOBt (0.60 g, 3.70 mmol) and Et3N (0.37 g, 3.70 mmol). The mixture was stirred at room temperature overnight then diluted with water and extracted with DCM. The organic layer was dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel using petroleum ether/ethyl acetate 5:1 (v:v) as eluent to give (E)-1-(2,3-dihydrobenzo[b][1,4]oxazin-4-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (230 mg, 32%). 1H-NMR (400 MHz, CDCl3) δ 3.88 (s, 3H), 3.91 (s, 3H), 4.08 (m, 2H), 4.37 (m, 2H), 6.86 (d, J=8.4 Hz, 1H), 6.90 (m, 1H), 6.92 (d, J=15.2 Hz, 1H), 6.96 (dd, J=8.0, 1.6 Hz, 1H), 6.99 (d, J=2.0 Hz, 1H), 7.08-7.13 (m, 2H), 7.20 (br d, J=7.6 Hz, 1H), 7.02 (d, J=15.6 Hz, 1H); LC-MS (ES-API); rt 8.72 min; m/z calculated for C19H19NO4 [M+H]+ 326.1, found 326.1.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6388d268aa4e47ac816f760d320825f1
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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