3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 118195073, compound

HRID 924114Notes

Reaction equation

HRID 924114 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])[F:18])=[CH:12][CH:11]=1)=[O:8].[F:28][C:29]1[C:30]([NH2:44])=[N:31][CH:32]=[C:33](B2OC(C)(C)C(C)(C)O2)[CH:34]=1>>[NH2:44][C:30]1[N:31]=[CH:32][C:33]([C:2]2[C:3]([N:22]3[CH2:26][CH2:25][C@@H:24]([OH:27])[CH2:23]3)=[N:4][CH:5]=[C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:18])([F:20])[F:19])=[CH:12][CH:11]=3)=[O:8])[CH:21]=2)=[CH:34][C:29]=1[F:28]

Participants

3

Reactant 2

HCID 592520523-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 86702593(R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide

Product 1

HCID 118195073HCID 118195073, compound

Procedure

The title compound was prepared in an analogous fashion to that described in Example 169 using (R)-5-bromo-6-(3-hydroxypyrrolidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 35.1) and 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine to afford a white amorphous powder. HPLC (Condition 4) tR=4.37 min, UPLC-MS (Condition 3) tR=0.91 min, m/z=478.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.66-1.89 (m, 2H) 2.94 (d, J=11.34 Hz, 1H) 3.18-3.28 (m, 2H) 3.34-3.47 (m, 1H) 4.19 (br. s, 1H) 4.83 (d, J=3.13 Hz, 1H) 6.32 (s, 2H) 7.32 (d, J=8.99 Hz, 2H) 7.40 (d, J=11.73 Hz, 1H) 7.77 (s, 1H) 7.83 (d, J=8.99 Hz, 2H) 7.93 (m, J=2.30, 1.20 Hz, 1H) 8.64-8.72 (m, 1H) 10.11 (s, 1H).

Workup

  1. customto afford a white amorphous powder

Sources & evidence

ORD record
ord-20ec49052c2c4adc95e259a481a9da2d
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

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