5-(4-Bromo-2-fluorophenyl)pyrazin-2-amine → 5-{4-[2-(Cyclobutyloxy)pyridin-3-yl]-2-fluorophenyl}pyrazin-2-amine

HRID 1523927Notes

Reaction equation

HRID 1523927 reaction equation
[CH:1]1([O:5][C:6]2[C:11](B(O)O)=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1.Br[C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=2)=[C:18]([F:29])[CH:17]=1>>[CH:1]1([O:5][C:6]2[C:11]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[N:23]=[CH:24][C:25]([NH2:28])=[N:26][CH:27]=4)=[C:18]([F:29])[CH:17]=3)=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amineHCID 90313666HCID 90313666, compound

Product 1

HCID 903137765-{4-[2-(Cyclobutyloxy)pyridin-3-yl]-2-fluorophenyl}pyrazin-2-amine

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using (2-(cyclobutoxy)pyridin-3-yl)boronic acid and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C19H17FN4O, 336.14; m/z found, 337.1 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.63-8.57 (m, 1H), 8.17-8.10 (m, 2H), 8.01-7.92 (m, 1H), 7.66 (dd, J=1.9, 7.4, 1H), 7.52-7.43 (m, 2H), 7.00-6.93 (m, 1H), 5.38-5.22 (m, 1H), 4.67 (s, 2H), 2.57-2.37 (m, 2H), 2.26-2.05 (m, 2H), 1.90-1.61 (m, 2H).

Sources & evidence

ORD record
ord-c4bbaa5832724439be8a7e21bde2a1ce
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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