Quinoxalin-6-ylboronic acid → (R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(quinoxalin-6-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 923882Notes

Reaction equation

HRID 923882 reaction equation
Cl[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:28]1[C:37]2[C:32](=[CH:33][C:34](B(O)O)=[CH:35][CH:36]=2)[N:31]=[CH:30][CH:29]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:3]2[C:2]([C:35]3[CH:36]=[C:37]4[C:32](=[CH:33][CH:34]=3)[N:31]=[CH:30][CH:29]=[N:28]4)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 45073596Quinoxalin-6-ylboronic acidHCID 89907107(R)-5-chloro-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 89908316(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(quinoxalin-6-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 46 using (R)-5-chloro-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 38.1) and quinoxalin-6-ylboronic acid. LC-MS (Condition 6) tR=1.64 min, m/z=496.0 [M+H]+.

Sources & evidence

ORD record
ord-ebe96521289d4fe7a893d9c5c7076057
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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