4-Methoxyphenylacetic Acid → N-(6-methoxyisoquinolin-3-yl)-2-(4-methoxyphenyl)acetamide

HRID 1672488

Reaktionsgleichung

Reaktionsgleichung von HRID 1672488
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(Cl)(=O)C(Cl)=O.[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[N:26][C:25]([NH2:31])=[CH:24]2.CCN(CC)CC>C1COCC1.CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[N:26][C:25]([NH:31][C:10](=[O:12])[CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)=[CH:24]2

Komponenten

7

Edukt 4

HCID 76904-Methoxyphenylacetic AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 233211576-Methoxyisoquinolin-3-amine

Produkt 1

HCID 58082419N-(6-methoxyisoquinolin-3-yl)-2-(4-methoxyphenyl)acetamideAusbeute 27,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (4-methoxyphenyl)acetic acid (166.2 mg, 0.86 mmol) in 5 ml of anhydrous THF were added oxalyl chloride (126.9 mg, 4.3 mmol) and 100 ul of DMF. A vigorous effervescence occurred. Within 1-4 minutes the effervescence stopped and the mixture was stirred for 30 minutes at room temperature. Then the 6-methoxyisoquinolin-3-amine (150.0 mg, 0.86 mmol) and Et3N (0.86 mmol) were added. The reaction was stirred at the ambient temperature over 16 hours. The reaction was monitored by LC/MS that showed no more start material left. The reaction crude was purified by a silica gel column to give product 75.7 mg (yield 27.3%). 1H NMR (400 MHz, DMSO-d6) ppm 3.68 (s, 2H), 3.72 (s, 3H), 3.89 (s, 3H), 6.89 (d, J=8.81 Hz, 2H), 7.14 (dd, J=8.94, 2.39 Hz, 1H), 7.26 (d, J=2.27 Hz, 1H), 7.30 (d, J=8.81 Hz, 2H), 7.95 (d, J=9.06 Hz, 1H), 8.32 (s, 1H), 8.98 (s, 1H), 10.73 (s, 1H). HRMS: m/z 323.13882 [M+H]+), calc. 323.13902. MS m/z, (APCI); 323.2 ([M+H]+).

Aufarbeitung

  1. stirringThe reaction was stirred at the ambient temperature over 16 hours
  2. waitleft
  3. customThe reaction crude
  4. customwas purified by a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-0eedebc388d54154bb1f71413338b6b5
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998978B2

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