Triethylamine → (Z)-methyl 2-(2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetamido)benzoate

HRID 2175717Notes

Reaction equation

HRID 2175717 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[NH:8][CH2:7]/[C:6]/2=[CH:16]\[C:17]([OH:19])=O.[NH2:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.CCN(CC)CC>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[C:9](=[O:15])[NH:8][CH2:7]/[C:6]/2=[CH:16]\[C:17]([NH:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24])=[O:19]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67088117(Z)-2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetic acid

Product 1

HCID 67087896(Z)-methyl 2-(2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetamido)benzoateYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (Z)-2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetic acid (789 mg, 3 mmol), methyl 2-aminobenzoate (544 mg, 3.6 mmol), HOBt (587 mg, 3.6 mmol), EDCl (688 mg, 3.6 mmol) and DMAP (439 mg, 3.6 mmol) in dry DMF (30 mL) was added Et3N (2 mL, 15 mmol) dropwise at room temperature. The resulting mixture was stirred at room temperature overnight then the reaction was quenched with water and extracted with DCM. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated to give the crude product which was purified by flash chromatography using DCM/MeOH 40:1 (v:v) as eluent to give (Z)-methyl 2-(2-(6,7-dimethoxy-1-oxo-2,3-dihydroisoquinolin-4(1H)-ylidene)acetamido)benzoate (280 mg, 80%) LC-MS (ES-API); rt 8.39 min; m/z calculated for C21H20N2O6 [M+Na]+ 419.1, found 419.1.

Workup

  1. customthe reaction was quenched with water
  2. extractionextracted with DCM
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto give the crude product which
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-b20d025a40b846f7beff868ae7cfe6f0
Source dataset
uspto-grants-2015_06
Patent number
US09062076B2

Reaction notes

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