(Pyrimidin-5-yl)boronic acid → HCID 89908230, compound

HRID 924083Notes

Reaction equation

HRID 924083 reaction equation
Br[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])[CH3:18])=[CH:12][CH:11]=1)=[O:8].[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1>>[F:19][C:17]([F:20])([O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:32]3[CH:33]=[N:28][CH:29]=[N:30][CH:31]=3)[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1)[CH3:18]

Participants

3

Reactant 2

HCID 2795193(Pyrimidin-5-yl)boronic acidHCID 86702628(R)-5-Bromo-N-(4-(1,1-difluoroethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide

Product 1

HCID 89908230HCID 89908230, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 185 using (R)-5-bromo-N-(4-(1,1-difluoroethoxy)phenyl)-6-(3-hydroxypyrrolidin-1-yl)nicotinamide (Stage 215.1) and pyrimidin-5-ylboronic acid to afford an off-white foam. HPLC (Condition 4) tR=4.28 min, UPLC-MS (Condition 3) tR=0.84 min, m/z=442.4 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.74 (m, J=4.30 Hz, 1H) 1.81-1.99 (m, 4H) 2.87 (d, J=11.34 Hz, 1H) 3.21 (m, J=11.30, 4.70 Hz, 2H) 3.37 (m, J=7.00 Hz, 1H) 4.15-4.24 (m, 1H) 4.86 (d, J=3.52 Hz, 1H) 7.16 (d, J=8.99 Hz, 2H) 7.74 (d, J=8.60 Hz, 2H) 8.08 (d, J=1.95 Hz, 1H) 8.77 (d, J=1.00 Hz, 1H) 8.87 (s, 2H) 9.18 (s, 1H) 10.06 (s, 1H).

Workup

  1. customto afford an off-white foam

Sources & evidence

ORD record
ord-b3492a0f636c40f1aad831a73ac70492
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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