2-Chloro-4-methoxybenzeneboronic acid → cis-(+/-)-4-{[5-(2-Chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}tetrahydrofuran-3-ol

HRID 1612309Notes

Reaction equation

HRID 1612309 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].[Cl:48][C:49]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:50]=1B(O)O>>[Cl:48][C:49]1[CH:54]=[C:53]([O:55][CH3:56])[CH:52]=[CH:51][C:50]=1[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]

Participants

4

Reactant 3

HCID 27733302-Chloro-4-methoxybenzeneboronic acidHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-olHCID 86588877cis-(+/-)-4-[(5-Bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

Product 1

HCID 86588878cis-(+/-)-4-{[5-(2-Chloro-4-methoxyphenyl)-3,6-diethylpyrazin-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 cis-(+/−)-4-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol and 2-chloro-4-methoxyphenylboronic acid and making non-critical variations provided the title compound as a light yellow amorphous solid. IR (diffuse reflectance) 3420, 2969, 2935, 2873, 1604, 1568, 1482, 1439, 1397, 1393, 1287, 1229, 1204, 1181, 1044 cm−1; OAMS supporting ions at: ESI+ 378.1; MS (EI) m/z 377 (M+); HRMS (FAB) calcd for C19H24CLN3O3+H1 378.1584, found 378.1566. Anal. Calcd for C19H24ClN3O3: C, 60.39; H, 6.40; N, 11.12. Found: C, 59.97; H, 6.46; N, 10.99.

Sources & evidence

ORD record
ord-f8d1e39011d94d19a02b5495dfc39465
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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