3-Fluoro-4-hydrazinylbenzonitrile → N-[6-[2-(4-Cyano-2-fluoro-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

HRID 1497804Notes

Reaction equation

HRID 1497804 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[C:8]([CH3:30])=[C:9]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[C:10]2[N:11]([N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[N:15]=2)[CH:12]=1)=O.[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[NH:41][NH2:42])[C:36]#[N:37]>>[C:36]([C:35]1[CH:38]=[CH:39][C:40]([N:41]2[C:5]([C:7]3[C:8]([CH3:30])=[C:9]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:28])([F:29])[F:27])[CH:21]=4)[C:10]4[N:11]([N:13]=[C:14]([NH:16][C:17](=[O:19])[CH3:18])[N:15]=4)[CH:12]=3)=[CH:4][CH:3]=[N:42]2)=[C:33]([F:32])[CH:34]=1)#[N:37]

Participants

3

Reactant 2

HCID 227622323-Fluoro-4-hydrazinylbenzonitrileHCID 86708112N-[6-(3-Dimethylamino-acryloyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

Product 1

HCID 73052395N-[6-[2-(4-Cyano-2-fluoro-phenyl)-2H-pyrazol-3-yl]-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide

Procedure

The title compound was prepared from N-[6-(3-dimethylamino-acryloyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-acetamide (Int. 25, 85 mg, 0.197 mmol) and 3-fluoro-4-hydrazino-benzonitrile (45 mg, 0.298 mmol) using similar methods to those employed in Example 40, Step 4 and Example 26, Step 1 (22 mg).

Sources & evidence

ORD record
ord-50b2a57c70294de2be65c540a46bfc2d
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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