(4-Methoxy-2-methylphenyl)boronic acid → N-(2,3-dihydro-1H-inden-1-yl)-5-(4-methoxy-2-methylphenyl)-3,6-dimethylpyrazin-2-amine

HRID 1612142Notes

Reaction equation

HRID 1612142 reaction equation
ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.Br[C:31]1[N:32]=[C:33]([CH3:48])[C:34]([NH:38][CH:39]2[C:47]3[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=3)[CH2:41][CH2:40]2)=[N:35][C:36]=1[CH3:37].[CH3:49][C:50]1[CH:55]=[C:54]([O:56][CH3:57])[CH:53]=[CH:52][C:51]=1B(O)O>>[CH:39]1([NH:38][C:34]2[C:33]([CH3:48])=[N:32][C:31]([C:51]3[CH:52]=[CH:53][C:54]([O:56][CH3:57])=[CH:55][C:50]=3[CH3:49])=[C:36]([CH3:37])[N:35]=2)[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40]1

Participants

4

Reactant 3

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 221474215-bromo-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-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 22147413N-(2,3-dihydro-1H-inden-1-yl)-5-(4-methoxy-2-methylphenyl)-3,6-dimethylpyrazin-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-bromo-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-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 1.92, 2.17, 2.26, 2.39, 2.80, 2.98, 3.07, 3.85, 4.54, 5.82, 6.84, 7.15, 7.30, 7.41; MS (ESI+) for C23H25N3O1 m/z 360.4 (M+H)+.

Sources & evidence

ORD record
ord-5a990747e1524a6ab798cc4e79833dad
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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