1-(p-Chlorophenyl)cyclopropanecarbonitrile → 1-{4-[8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarbonitrile

HRID 2273010Notes

Reaction equation

HRID 2273010 reaction equation
Cl[C:2]1[C:3]2[N:4]([N:8]=[C:9]([NH2:11])[N:10]=2)[CH:5]=[CH:6][N:7]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[N:22][NH:23][CH:24]=2)O1.Cl[C:27]1[CH:32]=[CH:31][C:30]([C:33]2([C:36]#[N:37])[CH2:35][CH2:34]2)=[CH:29][CH:28]=1>>[NH:23]1[CH:24]=[C:20]([C:2]2[C:3]3[N:4]([N:8]=[C:9]([NH:11][C:27]4[CH:32]=[CH:31][C:30]([C:33]5([C:36]#[N:37])[CH2:34][CH2:35]5)=[CH:29][CH:28]=4)[N:10]=3)[CH:5]=[CH:6][N:7]=2)[CH:21]=[N:22]1

Participants

4

Reactant 3

HCID 986661-(p-Chlorophenyl)cyclopropanecarbonitrileHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 772310108-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-amine

Product 1

HCID 717218221-{4-[8-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamino]-phenyl}-cyclopropanecarbonitrile

Procedure

8-Chloro-[1,2,4]triazolo[1,5-a]pyrazin-2-ylamine is reacted first with 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole using general procedure 1 and then with 1-(4-chlorophenyl)-1-cyclopropanecarbonitrile following general procedure 2.

Sources & evidence

ORD record
ord-ec4e3d00efad44f6a82af7f20c439755
Source dataset
uspto-grants-2015_09
Patent number
US09120804B2

Reaction notes

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