1,2-Dichloroethane → 3-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide

HRID 418340

Reaktionsgleichung

Reaktionsgleichung von HRID 418340
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([OH:9])=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH2:29][CH2:30][C:31]1[CH:32]=[C:33]([CH:48]=[CH:49][CH:50]=1)[C:34]([NH:36][C:37]1[CH:46]=[C:45]2[C:40]([CH2:41][CH2:42][N:43]([CH3:47])[CH2:44]2)=[CH:39][CH:38]=1)=[O:35]>CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH3:14])[C:7]([NH:29][CH2:30][C:31]1[CH:50]=[CH:49][CH:48]=[C:33]([C:34](=[O:35])[NH:36][C:37]2[CH:46]=[C:45]3[C:40]([CH2:41][CH2:42][N:43]([CH3:47])[CH2:44]3)=[CH:39][CH:38]=2)[CH:32]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 591908413-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamideHCID 666490683-Chloro-4-methoxybenzoic acid dihydrochloride

Produkt 1

HCID 591908573-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-4-methoxybenzoic acid dihydrochloride (29 mg, 150 mmol), EDC (30 mg, 150 mmol), HOBt (22 mg, 150 mmol), and TEA (0.057 mL, 408 mmol) in anhydrous DMF (5 mL) was stirred at room temperature for 30 min. To this was added 3-aminomethyl-N-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-yl)-benzamide. (50 mg, 136 mmol) and the solution stirred at room temperature for 24 h. The reaction was diluted EtOAc (100 mL) and quenched with sat. NH4Cl (100 mL). The organic fraction was dried (Na2SO4). The residue was purified by flash chromatography using a methanol/methylene chloride gradient to provide 31 mg of 3-chloro-4-methoxy-N-[3-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-7-ylcarbamoyl)-benzyl]-benzamide. MS, electrospray, 464 (M+H).

Aufarbeitung

  1. customquenched with sat. NH4Cl (100 mL)
  2. dry with materialThe organic fraction was dried (Na2SO4)
  3. customThe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0de0ffccb47347d3bd615425be5c317b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093266B2

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