(4-Methoxy-2-methylphenyl)boronic acid → trans-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

HRID 1612302Notes

Reaction equation

HRID 1612302 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]([CH2:46][CH3:47])[C:34]([NH:39][C@@H:40]2[CH2:44][O:43][CH2:42][C@H:41]2[OH:45])=[N:35][C:36]=1[CH2:37][CH3:38].[CH3:48][C:49]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:50]=1B(O)O>>[CH2:46]([C:33]1[C:34]([NH:39][C@@H:40]2[CH2:44][O:43][CH2:42][C@H:41]2[OH:45])=[N:35][C:36]([CH2:37][CH3:38])=[C:31]([C:50]2[CH:51]=[CH:52][C:53]([O:55][CH3:56])=[CH:54][C:49]=2[CH3:48])[N:32]=1)[CH3:47]

Participants

4

Reactant 3

HCID 2773486(4-Methoxy-2-methylphenyl)boronic acidHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-olHCID 86588872trans-(+/-)-4-[(5-Bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

Product 1

HCID 86588873trans-(+/-)-4-{[3,6-Diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-ol

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 trans-(+/−)-4-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol and 2-methyl-4-methoxyphenylboronic acid and making non-critical variations provided the title compound as a light yellow solid. IR (diffuse reflectance) 3363, 1603, 1571, 1490, 1447, 1393, 1303, 1233, 1208, 1177, 1170, 1103, 1059, 887, 849 cm−1; OAMS supporting ions at: ESI+ 358.1; MS (EI) m/z 357 (M+); HRMS (FAB) calcd for C20H27N3O3+H1 358.2130, found 358.2142.

Sources & evidence

ORD record
ord-decd676da8b64ea5bd7bd980dbd44512
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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