(4-Methoxy-2-methylphenyl)boronic acid → 5-(4-methoxy-2-methylphenyl)-3,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine

HRID 1824060Notes

Reaction equation

HRID 1824060 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.ClC1C=C(Cl)C=CC=1[C:38]1[N:39]=[C:40]([CH3:56])[C:41]([NH:45][CH:46]2[C:55]3[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=3)[CH2:49][CH2:48][CH2:47]2)=[N:42][C:43]=1[CH3:44].[CH3:57][C:58]1[CH:63]=[C:62]([O:64][CH3:65])[CH:61]=[CH:60][C:59]=1B(O)O>>[CH3:65][O:64][C:62]1[CH:61]=[CH:60][C:59]([C:38]2[N:39]=[C:40]([CH3:56])[C:41]([NH:45][CH:46]3[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[CH2:49][CH2:48][CH2:47]3)=[N:42][C:43]=2[CH3:44])=[C:58]([CH3:57])[CH:63]=1

Participants

4

Reactant 3

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 102161225-(2,4-dichlorophenyl)-3,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amineHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 103092735-(4-methoxy-2-methylphenyl)-3,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine

Procedure

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting 5-(2,4-dichlorophenyl)-3,6-dimethyl-N-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrazin-2-amine and 2-methyl-4-methoxy phenyl boronic acid, and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.81, 2.01, 2.06, 2.13, 2.22, 2.77, 3.71, 4.38, 5.39, 6.70, 7.09, 7.31; 13C NMR (CDCl3) δ 20.07, 20.47, 20.54, 22.09, 29.96, 30.28, 48.94, 55.68, 111.58, 116.05, 126.64, 127.57, 129.43, 129.60, 131.24, 132.37, 135.83, 138.31, 138.56, 138.74, 140.69, 147.04, 150.92, 159.51; HRMS (ESI+) for C24H27N3O1 m/z cald 374.2232 (M+H)+ found 374.2226.

Sources & evidence

ORD record
ord-b1038f91c1cb4812b451bfb04acfab50
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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