2,6-Dimethoxybenzoyl chloride → (8-Benzooxazol-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-(2,6-dimethoxy-phenyl)-methanone

HRID 1193135Notes

Reaction equation

HRID 1193135 reaction equation
[CH:1]12[N:8]([C:9]3[O:10][C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[N:13]=3)[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.[C@@H]12N(C3C=NC4C(=CC=CC=4)N=3)C[C@@H]1CCNC2.[CH3:36][O:37][C:38]1[CH:46]=[CH:45][CH:44]=[C:43]([O:47][CH3:48])[C:39]=1[C:40](Cl)=[O:41].C1(C2C=CC=CC=2)C(C(Cl)=O)=CC=CC=1>>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[N:8]1[CH:1]2[CH:6]([CH2:5][CH2:4][N:3]([C:40]([C:39]3[C:43]([O:47][CH3:48])=[CH:44][CH:45]=[CH:46][C:38]=3[O:37][CH3:36])=[O:41])[CH2:2]2)[CH2:7]1

Participants

5

Reactant 4

HCID 748102,6-Dimethoxybenzoyl chlorideHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 671166542-(3,8-Diaza-bicyclo[4.2.0]oct-8-yl)-benzooxazoleHCID 68156918(1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)quinoxaline

Product 1

HCID 67116558(8-Benzooxazol-2-yl-3,8-diaza-bicyclo[4.2.0]oct-3-yl)-(2,6-dimethoxy-phenyl)-methanone

Procedure

The title compound was prepared in a manner analogous to Example 5, substituting 2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-benzooxazole (Intermediate 7) for (1R,6S)-2-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-quinoxaline and 2,6-dimethoxy benzoyl chloride for biphenyl-2-carbonyl chloride. MS (ESI) mass calcd. for C22H23N3O4, 393.44; m/z found 394.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.54-7.27 (m, 2H), 7.25-7.06 (m, 3H), 6.57-6.01 (m, 2H), 5.12-4.00 (m, 5H), 3.98-3.33 (m, 7H), 3.20-2.94 (m, 2H), 2.24-1.72 (m, 2H).

Sources & evidence

ORD record
ord-22aed04d05a548849716537953e2a4f1
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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