[2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine → 3-Chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-5-nitrobenzonitrile

HRID 626773Notes

Reaction equation

HRID 626773 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[N:12]1[CH:29]=[C:15]2[C:16]([NH:21][C:22]3[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=3)=[N:17][CH:18]=[C:19]([F:20])[C:14]2=[N:13]1.Br[C:31]1C2=CN(C3C(Cl)=CC([N+]([O-])=O)=CC=3C#N)N=C2C(F)=C[N:32]=1>>[Cl:11][C:4]1[C:3]([N:12]2[CH:29]=[C:15]3[C:16]([NH:21][C:22]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24][N:23]=4)=[N:17][CH:18]=[C:19]([F:20])[C:14]3=[N:13]2)=[C:2]([CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=1)[C:31]#[N:32]

Participants

3

Reactant 2

HCID 69671549[2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amineHCID 866970702-(4-Bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chloro-5-nitrobenzonitrile

Product 1

HCID 696719523-Chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)-pyrazolo[4,3-c]pyridin-2-yl]-5-nitrobenzonitrileYield 20%

Conditions

Temperature
80 °C

Procedure

Following the procedure described for [2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridin-4-yl]-(6-methylpyrimidin-4-yl)-amine, 2-(4-bromo-7-fluoropyrazolo[4,3-c]pyridin-2-yl)-3-chloro-5-nitrobenzonitrile was heated at 80° C. overnight to afford the title compound as a pale yellow solid (43 mg, 20% yield). LCMS (Method C): RT=2.56 min, m/z: 425 [M+H+].

Sources & evidence

ORD record
ord-1ba86eef151948a39d086d46246352b6
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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