(Pyrimidin-5-yl)boronic acid → (R)-N-(4-(2-Chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

HRID 924134Notes

Reaction equation

HRID 924134 reaction equation
Br[C:2]1[C:3]([N:24]2[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]2)=[N:4][CH:5]=[C:6]([CH:23]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:22])([F:21])[C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:30]1[CH:35]=[C:34](B(O)O)[CH:33]=[N:32][CH:31]=1>>[Cl:20][C:17]([F:19])([F:18])[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:23]=[C:2]([C:34]3[CH:35]=[N:30][CH:31]=[N:32][CH:33]=3)[C:3]([N:24]3[CH2:28][CH2:27][C@@H:26]([OH:29])[CH2:25]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1)([F:22])[F:21]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702630(R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 118195323(R)-N-(4-(2-Chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 169 using (R)-5-bromo-N-(4-(2-chloro-1,1,2,2-tetrafluoroethyl)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 278.1) and pyrimidin-5-ylboronic acid to afford an amorphous white powder. HPLC (Condition 4) tR=5.21 min, UPLC-MS (Condition 3) tR=0.99 min, m/z=496.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.77 (m, 1H) 1.78-1.89 (m, 1H) 2.82-2.92 (m, 1H) 3.14-3.26 (m, 2H) 3.32-3.42 (m, 1H) 4.15-4.26 (m, 1H) 4.87 (d, J=3.13 Hz, 1H) 7.63 (d, J=8.99 Hz, 2H) 7.97 (d, J=8.60 Hz, 2H) 8.10 (dd, J=2.35, 0.78 Hz, 1H) 8.79 (dd, J=2.35, 0.78 Hz, 1H) 8.88 (d, J=0.78 Hz, 2H) 9.18 (d, J=0.78 Hz, 1H) 10.31 (s, 1H).

Workup

  1. customto afford an amorphous white powder

Sources & evidence

ORD record
ord-372e77c286ac4229b34554bff2921d93
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…