4-Aminopyridine → 4-Benzylamino-6-(pyridin-4-ylamino) pyridine-3-carboxyamide

HRID 2035545Notes

Reaction equation

[CH2:1]([NH:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][C:10]=1[CH2:16][C:17]([NH2:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NCC1CCCN1CC1C=CC=CC=1.[NH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([NH:34][C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)[N:12]=[CH:11][C:10]=1[CH2:16][C:17]([NH2:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

25 mg of 4-benzylamino-6-chloropyridine-3-carboxyamide (the compound of Example 1) was dissolved in 0.5 ml of toluene, to which 13.5 mg of 4-aminopyridine, 2 mg of palladium (II) acetate, 248 mg of potassium carbonate and 11 mg of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl were added, and stirred at 100° C. for 28 hours. After cooling, the insoluble substances were filtered off, the filtered product was washed with toluene, combined with the filtrate, and the solvent was evaporated. The residue obtained was purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain 4.8 mg (yield 16%) of the title compound as a slight yellow crystalline powder.

Workup

additionwere added
temperatureAfter cooling
filtrationthe insoluble substances were filtered off
washthe filtered product was washed with toluene
customthe solvent was evaporated
customThe residue obtained
customwas purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record: ord-31071e56a1de4f03a46aed7b444fcafc
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575153B2

Reaction notes

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