B-[2-(Cyclohexyloxy)-3-pyridinyl]boronic acid → HCID 90312943, compound

HRID 1523925Notes

Reaction equation

HRID 1523925 reaction equation
[CH:1]1([O:7][C:8]2[C:13](B(O)O)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)=[C:20]([F:31])[CH:19]=1>>[CH:1]1([O:7][C:8]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[N:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=4)=[C:20]([F:31])[CH:19]=3)=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 73012461B-[2-(Cyclohexyloxy)-3-pyridinyl]boronic acidHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 90312943HCID 90312943, compound

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using (2-(cyclohexyloxy)pyridin-3-yl)boronic acid and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C21H21FN4O, 364.17; m/z found, 365.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.64-8.57 (m, 1H), 8.18-8.10 (m, 2H), 8.00-7.92 (m, 1H), 7.70-7.63 (m, 1H), 7.52-7.43 (m, 2H), 6.94 (dd, J=5.0, 7.4, 1H), 5.26-5.16 (m, 1H), 4.66 (s, 2H), 2.05-1.91 (m, 2H), 1.82-1.68 (m, 2H), 1.66-1.24 (m, 6H).

Sources & evidence

ORD record
ord-5018bdbc1bdf447ab999f05e6dc6a3d4
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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