Chloropyrazine → 5-[3-Fluoro-2'-(pyrazin-2-ylsulfanyl)biphenyl-4-yl]pyrazin-2-amine hydrochloride

HRID 1523849Notes

Reaction equation

HRID 1523849 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([SH:20])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][C:9]=2[F:21])=[N:6][CH:7]=1.[Cl:22][C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1>>[ClH:22].[F:21][C:9]1[CH:10]=[C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[S:20][C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)[CH:12]=[CH:13][C:8]=1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 73277ChloropyrazineHCID 1364991434'-(5-Aminopyrazin-2-yl)-5'-fluorobiphenyl-2-thiol

Product 1

HCID 903142105-[3-Fluoro-2'-(pyrazin-2-ylsulfanyl)biphenyl-4-yl]pyrazin-2-amine hydrochloride

Procedure

The title compound was prepared using analogous conditions to those described in Example 213 utilizing 4′-(5-aminopyrazin-2-yl)-3′-fluoro-[1,1′-biphenyl]-2-thiol and 2-chloropyrazine. MS (ESI): mass calcd. for C20H14FN5S, 375.10; m/z found, 375.9 [M+H]+. 1H NMR (400 MHz, CD3OD) δ 8.26-8.24 (m, 3H), 8.18 (d, J=2.6, 1H), 8.08 (d, J=1.4, 1H), 7.84 (m, 1H), 7.77-7.69 (m, 1H), 7.64-7.55 (m, 1H), 7.55-7.46 (m, 2H), 7.27-7.14 (m, 2H).

Sources & evidence

ORD record
ord-85132658addd46009fbef6aaee1e4aa7
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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