4-Cyanophenyl isocyanate → (1R,3S)-1-(4-bromophenyl)-N-(4-cyanophenyl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide

HRID 445326

Reaktionsgleichung

Reaktionsgleichung von HRID 445326
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@H:10]([CH3:18])[NH:9]2)=[CH:4][CH:3]=1.[N:19]([C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1)=[C:20]=[O:21]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@H:10]([CH3:18])[N:9]2[C:20]([NH:19][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[O:21])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 1703804-Cyanophenyl isocyanateHCID 59536341(1R,3S)-1-(4-bromophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline

Produkt 1

HCID 59536325(1R,3S)-1-(4-bromophenyl)-N-(4-cyanophenyl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S)-1-(4-bromophenyl)-3-methyl-1,2,3,4-tetrahydroisoquinoline (50 mg, 165 example 81, step 2) in CH2Cl2 (1.0 mL) at RT was added 4-isocyanatobenzonitrile (37 mg, 256 μmol). The reaction was stirred 5 h and directly purified by reverse phase HPLC to give (1R,3S)-1-(4-bromophenyl)-N-(4-cyanophenyl)-3-methyl-3,4-dihydroisoquinoline-2(1H)-carboxamide as a white solid. MS (ESI pos. ion) m/z: 446, 448 (M+1).

Aufarbeitung

  1. customdirectly purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-2131b3a11c0d4dfea34d85bb2b4fb56d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476297B2

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