(2-Aminopyrimidin-5-yl)boronic acid → 5-(2-Aminopyrimidin-5-yl)-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

HRID 923888Notes

Reaction equation

HRID 923888 reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:26][CH2:25][CH2:24][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].[NH2:27][C:28]1[N:33]=[CH:32][C:31](B(O)O)=[CH:30][N:29]=1>>[NH2:27][C:28]1[N:33]=[CH:32][C:31]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:4][CH:5]=[C:6]([CH:21]=2)[C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)=[O:8])=[CH:30][N:29]=1

Participants

3

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 899068675-bromo-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 899079245-(2-Aminopyrimidin-5-yl)-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 66 using 5-bromo-6-(pyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 67.1) and (2-aminopyrimidin-5-yl)boronic acid to afford a white solid. UPLC-MS (Condition 3) tR=0.99 min, m/z=445.3 [M+H]+, m/z=443.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.75-1.84 (m, 4H) 3.18-3.26 (m, 4H) 6.77 (s, 2H) 7.34 (d, J=8.31 Hz, 2H) 7.86 (d, J=9.29 Hz, 2H) 7.95 (d, J=2.45 Hz, 1H) 8.27 (s, 2H) 8.71 (d, J=2.45 Hz, 1H) 10.12 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-803908f123274e9797454d27e13bc282
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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