2-Chloro-4-methoxybenzeneboronic acid → benzyl (3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate

HRID 1824209Notes

Reaction equation

HRID 1824209 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]([CH2:56][CH3:57])[C:34]([NH:39][C@H:40]2[C@@H:44]([OH:45])[CH2:43][N:42]([C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH2:41]2)=[N:35][C:36]=1[CH2:37][CH3:38].[Cl:58][C:59]1[CH:64]=[C:63]([O:65][CH3:66])[CH:62]=[CH:61][C:60]=1B(O)O>>[Cl:58][C:59]1[CH:64]=[C:63]([O:65][CH3:66])[CH:62]=[CH:61][C:60]=1[C:31]1[N:32]=[C:33]([CH2:56][CH3:57])[C:34]([NH:39][C@H:40]2[C@@H:44]([OH:45])[CH2:43][N:42]([C:46]([O:48][CH2:49][C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[O:47])[CH2:41]2)=[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 58583437benzyl(3R,4S)-3-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 58583248benzyl (3R,4S)-3-{[5-(2-chloro-4-methoxyphenyl)-3,6-diethylpyrazin-2-yl]amino}-4-hydroxypyrrolidine-1-carboxylate

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 benzyl(3R,4S)-3-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate and 2-chloro-4-methoxy phenyl boronic acid, and making non-critical variations provided the title compound as a oil: 1H NMR (DMSO-d6) δ) 1.06, 2.35, 2.67, 3.51, 3.57, 3.62, 3.82, 4.35, 4.46, 5.08, 5.42, 5.95, 6.98, 7.11, 7.24, 7.38; IR (diffuse reflectance) 2968, 2351 (w), 2339 (w), 2063 (w), 1951 (w), 1700 (s,b), 1681 (s), 1568 (s), 1482 (s), 1428 (s,b), 1422 (s), 1397, 1359 (s), 1287, 1229, cm−1 HRMS (FAB) calcd for C27H31ClN4O4+H 511.2112, found 511.2115.

Sources & evidence

ORD record
ord-d866f467d4c844db8469475e86b2df06
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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