2-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine → (R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(2-methylpyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

HRID 923832Notes

Reaction equation

HRID 923832 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[N:22]1[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=1)=[O:6].[CH3:28][C:29]1[N:34]=[CH:33][C:32](B2OC(C)(C)C(C)(C)O2)=[CH:31][N:30]=1>>[OH:27][C@@H:24]1[CH2:25][CH2:26][N:22]([C:21]2[CH:20]=[CH:19][C:4]([C:5]([NH:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:10][CH:9]=3)=[O:6])=[CH:3][C:2]=2[C:32]2[CH:31]=[N:30][C:29]([CH3:28])=[N:34][CH:33]=2)[CH2:23]1

Participants

3

Reactant 2

HCID 457872822-Methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 86702591(R)-3-bromo-4-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Product 1

HCID 118195242(R)-4-(3-Hydroxypyrrolidin-1-yl)-3-(2-methylpyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 1 using (R)-3-bromo-4-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 2.1) and 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine to afford a white solid. UPLC-MS (condition 1) tR=2.46 min, m/z=459.1-460.1 [M+H]+, m/z=457.2-458.2 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.76 (d, J=3.91 Hz, 1H) 1.82-1.93 (m, 1H) 2.65-2.72 (m, 1H) 2.68 (s, 3H) 3.00-3.11 (m, 2H) 3.18-3.27 (m, 1H) 4.17-4.25 (m, 1H) 4.86 (d, J=3.67 Hz, 1H) 6.96 (d, J=8.80 Hz, 1H) 7.33 (d, J=8.56 Hz, 2H) 7.81 (d, J=2.20 Hz, 1H) 7.83-7.88 (m, 2H) 7.92 (dd, J=8.80, 2.20 Hz, 1H) 8.73 (s, 2H) 10.08 (s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-f43f31af46af4ae8b8a9b420216d531e
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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