2,6-Dimethoxybenzoic Acid → (2,6-Dimethoxy-phenyl)-[8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone

HRID 1193134Notes

Reaction equation

HRID 1193134 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]3[CH:20]4[CH:15]([CH2:16][CH2:17][NH:18][CH2:19]4)[CH2:14]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC1C=C(C)N=C(N2[C@@H]3[C@@H](CCNC3)C2)N=1.[CH3:37][O:38][C:39]1[CH:47]=[CH:46][CH:45]=[C:44]([O:48][CH3:49])[C:40]=1[C:41](O)=[O:42].S1C=CC=C1C1C=CC=CC=1C(O)=O>>[CH3:49][O:48][C:44]1[CH:45]=[CH:46][CH:47]=[C:39]([O:38][CH3:37])[C:40]=1[C:41]([N:18]1[CH2:17][CH2:16][CH:15]2[CH:20]([N:13]([C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:12]=[CH:11][N:10]=3)[CH2:14]2)[CH2:19]1)=[O:42]

Participants

5

Reactant 4

HCID 151092,6-Dimethoxybenzoic AcidHCID 51056232-(Thiophen-2-yl)benzoic acidHCID 671167498-(4-Phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octaneHCID 68156939(1R,6S)-8-(4,6-Dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

Product 1

HCID 67116788(2,6-Dimethoxy-phenyl)-[8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]oct-3-yl]-methanone

Procedure

The title compound was prepared in a manner analogous to Example 1, substituting 8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 6) for (1R,6S)8-(4,6-dimethyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane and 2,6-dimethoxy-benzoic acid for 2-thiophen-2-yl-benzoic acid. MS (ESI) mass calcd. for C25H26N4O3, 430.50; m/z found, 431.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.60-7.27 (m, 7H), 7.25-6.66 (m, 3H), 4.84-2.46 (m, 12H), 2.18-1.15 (m, 4H).

Sources & evidence

ORD record
ord-a9cb0ee8bc7a4ecc894c5d6ce58daa0f
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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