HCID 46737875, compound → HCID 90313791, compound

HRID 1523928Notes

Reaction equation

HRID 1523928 reaction equation
CC1(C)C(C)(C)OB([C:9]2[C:10]([O:15][CH2:16][CH:17]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]3)=[N:11][CH:12]=[CH:13][CH:14]=2)O1.Br[C:31]1[CH:36]=[CH:35][C:34]([C:37]2[N:38]=[CH:39][C:40]([NH2:43])=[N:41][CH:42]=2)=[C:33]([F:44])[CH:32]=1>>[NH2:43][C:40]1[N:41]=[CH:42][C:37]([C:34]2[CH:35]=[CH:36][C:31]([C:9]3[C:10]([O:15][CH2:16][CH:17]4[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:18]4)=[N:11][CH:12]=[CH:13][CH:14]=3)=[CH:32][C:33]=2[F:44])=[N:38][CH:39]=1

Participants

3

Reactant 2

HCID 46737875HCID 46737875, compoundHCID 903128885-(4-Bromo-2-fluorophenyl)pyrazin-2-amine

Product 1

HCID 90313791HCID 90313791, compound

Procedure

The title compound was prepared using methods analogous to those described in Example 369 using tert-butyl 3-(((3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl)oxy)methyl)pyrrolidine-1-carboxylate and 5-(4-bromo-2-fluorophenyl)pyrazin-2-amine in Step B. MS (ESI): mass calcd. for C25H28FN5O3, 465.22; m/z found, 466.2 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 8.63-8.58 (m, 1H), 8.18-8.09 (m, 2H), 8.03-7.94 (m, 1H), 7.73-7.64 (m, 1H), 7.48-7.36 (m, 2H), 7.05-6.96 (m, 1H), 4.70 (s, 2H), 4.47-4.22 (m, 2H), 3.68-3.26 (m, 3H), 3.25-3.09 (m, 1H), 2.77-2.60 (m, 1H), 2.14-1.98 (m, 1H), 1.84-1.68 (m, 1H), 1.44 (s, 9H).

Sources & evidence

ORD record
ord-9f60856fd1a6422f82c61d1cf92829b8
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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