4-(Morpholin-4-yl)benzene-1,2-diamine → 6-[(2-Amino-5-cyanophenyl)amino]-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

HRID 2035542Notes

Reaction equation

HRID 2035542 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.O1CCN(C2C=CC(N)=C(N)C=2)CC1.[NH2:36][C:37]1[CH:42]=[C:41]([C:43]#[N:44])[CH:40]=[CH:39][C:38]=1[NH:45]C1N=CC(CC(N)=O)=C(NCC2C=C(F)C=C(F)C=2)C=1>>[NH2:45][C:38]1[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:37]=1[NH:36][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 141123324-(Morpholin-4-yl)benzene-1,2-diamineHCID 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-morpholino-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 1:1) was obtained as a red oil (yield 17%).

Sources & evidence

ORD record
ord-a1b2b2adac804b6e9f479d893d6ffb15
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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