Trimethyl orthoformate → 6-(5-cyano-1H-benzimidazol-1-yl)-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][C:3]=1[NH:10][C:11]1[N:16]=[CH:15][C:14]([CH2:17][C:18]([NH2:20])=[O:19])=[C:13]([NH:21][CH2:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[C:25]([F:30])[CH:24]=2)[CH:12]=1.N[C:32]1C=CC(C#N)=CC=1NC1N=CC(CC(N)=O)=C(NCC2C=C(F)C=C(F)C=2)C=1.C(OC)(OC)OC>>[C:8]([C:6]1[CH:5]=[CH:4][C:3]2[N:10]([C:11]3[N:16]=[CH:15][C:14]([CH2:17][C:18]([NH2:20])=[O:19])=[C:13]([NH:21][CH2:22][C:23]4[CH:24]=[C:25]([F:30])[CH:26]=[C:27]([F:29])[CH:28]=4)[CH:12]=3)[CH:32]=[N:1][C:2]=2[CH:7]=1)#[N:9]Participants
4
Reactant 3
Product 1
Procedure
From the 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 3:1) and trimethyl orthoformate in a manner similar to step 2 of Example 365, the title compound was obtained as a white solid (yield 45%).
Sources & evidence
- ORD record
- ord-a2b546bae12e46d5b0a73460dbafa222
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575153B2
Reaction notes
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