Potassium Carbonate → HCID 131730962, compound

HRID 2035501Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][NH:6][C:7]1[CH:12]=[C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[CH:16][CH:15]=2)[N:10]=[CH:9][C:8]=1[CH2:26][C:27]([NH2:29])=[O:28].Br[CH2:35][CH2:36][C:37]#[N:38].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:37]([CH2:36][CH2:35][N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:11]3[N:10]=[CH:9][C:8]([CH2:26][C:27]([NH2:29])=[O:28])=[C:7]([NH:6][CH2:5][C:4]4[CH:3]=[C:2]([F:1])[CH:32]=[C:31]([F:33])[CH:30]=4)[CH:12]=3)=[CH:19][CH:18]=2)[CH2:21][CH2:22]1)#[N:38]

Participants

Conditions

Temperature: 80 °C

Procedure

60 mg of 4-[(3,5-difluorobenzyl)amino]-6-{[4-(piperazin-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 221) was dissolved in 0.6 mL of N,N-dimethylformamide, to which 45 mg of 3-bromopropionitrile and 57 mg of potassium carbonate were added, and stirred at 80° C. for 4 hours. After cooling, the solvent was evaporated, the residue was dissolved in chloroform, and the insoluble substances were filtered off. Chloroform was evaporated and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1) to obtain 52 mg (77%) of the title compound as a light yellow crystalline powder.

Workup

additionwere added
temperatureAfter cooling
customthe solvent was evaporated
dissolutionthe residue was dissolved in chloroform
filtrationthe insoluble substances were filtered off
customChloroform was evaporated
customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=5:1)

Sources & evidence

ORD record: ord-bd21cad58e524ed0b31f3b7f3e2d7218
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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