2-Chloroquinoxaline → HCID 52915315, compound

HRID 2175037Notes

Reaction equation

HRID 2175037 reaction equation
[CH:1]12[N:8]([C:9]([C:11]3[C:16]([O:17][CH3:18])=[CH:15][CH:14]=[CH:13][C:12]=3[O:19][CH3:20])=[O:10])[CH2:7][CH:6]1[CH2:5][CH2:4][NH:3][CH2:2]2.[C:21]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)C=CC=C[C:22]=1[C:27]([N:29]1C2C(CCNC2)[CH2:30]1)=O.ClC1C=CC=CC=1C1N=CC=C[N:51]=1.ClC1C=NC2C(=CC=CC=2)N=1>>[CH3:18][O:17][C:16]1[CH:15]=[CH:14][CH:13]=[C:12]([O:19][CH3:20])[C:11]=1[C:9]([N:8]1[CH:1]2[CH:6]([CH2:5][CH2:4][N:3]([C:30]3[N:51]=[C:21]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[CH:22]=[CH:27][N:29]=3)[CH2:2]2)[CH2:7]1)=[O:10]

Participants

5

Reactant 4

HCID 2389382-ChloroquinoxalineHCID 10821528HCID 10821528, compoundHCID 67086559HCID 67086559, compound2×HCID 67086667HCID 67086667, compound

Product 1

HCID 52915315HCID 52915315, compound

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting substituting the trifluoro acetic acid salt of (3,8-diaza-bicyclo[4.2.0]oct-8-yl)-(2,6-dimethoxy-phenyl)-methanone (Intermediate 4) for biphenyl-2-yl-(3,8-diaza-bicyclo[4.2.0]oct-8-yl)-methanone and 2-chloro phenyl pyrimidine for 2-chloro quinoxaline. MS (ESI) mass calcd. for C25H26N4O3, 430.20; m/z found, 431.3 [M+H]+. 1H NMR (CDCl3): 8.64 (d, J=5.3, 0.75H), 8.42 (d, J=5.2, 0.25H), 8.11-8.00 (m, 2H), 7.65 (d, J=5.3, 0.75H), 7.58-7.37 (m, 4H), 7.23-7.11 (m, 0.75H), 6.95 (d, J=5.2, 0.75H), 6.54 (d, J=8.4, 0.75H), 5.33-4.76 (m, 0.5H), 4.60-4.20 (m, 1.5H), 4.09-3.04 (m, 9H), 3.00-2.72 (m, 1H), 2.25-1.80 (m, 2H), 1.75-1.60 (m, 2H).

Sources & evidence

ORD record
ord-d62907a7bb9642848575ed7f04808f2d
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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