Potassium Carbonate → 7-chloro-6-(4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 911371

Reaktionsgleichung

Reaktionsgleichung von HRID 911371
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].[Cl:20][C:21]1[CH:37]=[CH:36][C:24]2[CH2:25][CH2:26][N:27]([C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])[CH2:28][CH2:29][C:23]=2[C:22]=1OS(C(F)(F)F)(=O)=O.COC(=O)C1C=CC(CN)=CC=1>C1(C)C=CC=CC=1.O>[Cl:20][C:21]1[CH:37]=[CH:36][C:24]2[CH2:25][CH2:26][N:27]([C:30](=[O:35])[C:31]([F:32])([F:34])[F:33])[CH2:28][CH2:29][C:23]=2[C:22]=1[NH:12][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([C:4]([O:3][CH3:2])=[O:13])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 571728Methyl 4-(aminomethyl)benzoateHCID 2729253Methyl 4-(aminomethyl)benzoate hydrochlorideHCID 574477477-Chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethylsulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Produkt 1

HCID 576561767-chloro-6-(4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 22272177Toluene waterLösungsmittel

Versuchsvorschrift

Treat 4-aminomethyl-benzoic acid methyl ester hydrochloride (0.2 g, 0.71 mmol) with K2CO3 (1.0 g, 0.71 mmol) in a mixture of toluene/water (1:1, 2 mL). Separate the organic layer, dry over anhydrous Na2SO4 and use as a toluene solution for the next step. Use a method similar to the General Procedure 5-2, using 7-chloro-3-(2,2,2-trifluoroacetyl)-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.1 g, 0.24 mmol) and 4-aminomethyl-benzoic acid methyl ester (0.2 g, 0.71 mmol) to give 7-chloro-6-(4-methoxycarbonyl-benzylamino)-3-(2,2,2-trifluoroacetyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a colorless oil.

Aufarbeitung

  1. customSeparate the organic layer
  2. dry with materialdry over anhydrous Na2SO4 and use as a toluene solution for the next step

Quellen und Nachweise

ORD-Eintrag
ord-74df0fec5551454aa292e2dceac1de3c
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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