5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amine → HCID 90313939, compound

HRID 1523854Notes

Reaction equation

HRID 1523854 reaction equation
[F:1][C:2]1[CH:7]=[C:6](B2[O:12][C:11](C)(C)C(C)(C)O2)[CH:5]=[CH:4][C:3]=1[C:17]1[N:18]=[CH:19][C:20]([NH2:23])=[N:21][CH:22]=1.Br[C:25]1[CH:41]=[CH:40][CH:39]=[CH:38][C:26]=1[CH2:27][S:28]([N:31]1[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]1)(=[O:30])=[O:29]>>[CH:11]([OH:12])=[O:29].[NH2:23][C:20]1[N:21]=[CH:22][C:17]([C:3]2[CH:4]=[CH:5][C:6]([C:25]3[CH:41]=[CH:40][CH:39]=[CH:38][C:26]=3[CH2:27][S:28]([N:31]3[CH2:36][CH2:35][NH:34][C:33](=[O:37])[CH2:32]3)(=[O:30])=[O:29])=[CH:7][C:2]=2[F:1])=[N:18][CH:19]=1

Participants

3

Reactant 2

HCID 903122765-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-pyrazin-2-amineHCID 90314509HCID 90314509, compound

Product 1

HCID 90313939HCID 90313939, compound

Procedure

The title compound was prepared using analogous conditions to those described in Example 1 utilizing 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrazin-2-amine and 4-((2-bromobenzyl)sulfonyl)piperazin-2-one. MS (ESI): mass calcd. for C21H20FN5O3S, 441.13; m/z found, 441.9 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.41 (s, 1H), 8.08 (d, J=1.3, 1H), 7.96 (m, 1H), 7.70-7.62 (m, 1H), 7.52-7.28 (m, 5H), 4.48 (s, 2H), 3.63 (s, 2H), 3.25 (s, 4H).

Sources & evidence

ORD record
ord-9a627566b8094905833e879a04a91cf7
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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