(2-Bromophenyl)(morpholino)methanone → 3-Amino-6-[3-fluoro-2'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]pyrazine-2-carbonitrile

HRID 1523938Notes

Reaction equation

HRID 1523938 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9].[NH2:16][C:17]1[C:18]([C:39]#[N:40])=[N:19][C:20]([C:23]2[CH:28]=[CH:27][C:26](B3OC(C)(C)C(C)(C)O3)=[CH:25][C:24]=2[F:38])=[CH:21][N:22]=1>>[NH2:16][C:17]1[C:18]([C:39]#[N:40])=[N:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[O:9])=[CH:25][C:24]=2[F:38])=[CH:21][N:22]=1

Participants

3

Reactant 2

HCID 532184(2-Bromophenyl)(morpholino)methanoneHCID 903135533-Amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile

Product 1

HCID 903131463-Amino-6-[3-fluoro-2'-(morpholin-4-ylcarbonyl)biphenyl-4-yl]pyrazine-2-carbonitrile

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using (2-bromophenyl)(morpholino)methanone and 3-amino-6-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazine-2-carbonitrile. MS (ESI): mass calcd. for C22H18FN5O2, 403.14; m/z found, 404.1 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 7.45 (d, J=2.1, 1H), 6.71 (m, 1H), 6.32-6.21 (m, 3H), 6.17-6.10 (m, 2H), 6.07 (dd, J=12.4, 1.8, 1H), 2.40-2.22 (m, 3H), 2.13-2.03 (m, 2H), 1.86-1.77 (m, 1H), 1.62-1.49 (m, 2H).

Sources & evidence

ORD record
ord-c2266ce1066845cfaad99c6c2e7af4d2
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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