3,4-Diaminobenzonitrile → 6-[(2-Amino-5-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

HRID 2035539Notes

Reaction equation

HRID 2035539 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:3]=1.[C:22]([C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[C:26]([NH2:31])[CH:25]=1)#[N:23].NC1C=C(C#N)C=CC=1NC1N=CC(CC(N)=O)=C(NCC2C=C(F)C=C(F)C=2)C=1>>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:22]#[N:23])=[CH:25][C:26]=1[NH:31][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:3]=1

Participants

4

Reactant 3

HCID 7372853,4-DiaminobenzonitrileHCID 1317309496-Chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamideHCID 1317310046-[(2-Amino-4-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

Product 1

HCID 1317310036-[(2-Amino-5-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

Procedure

From 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) and 4-cyano-1,2-phenylenediamine in a manner similar to step 1 of Example 365, a mixture of 6-[(2-amino-4-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide and 6-[(2-amino-5-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (1H-NMR integral ratio 1:6) was obtained as a light yellow oil (yield 7%).

Sources & evidence

ORD record
ord-26be4c08adc84a90988d5ddb1044ac8d
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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