4-Aminopyridine → 1-[4-(methylamino)-6-(4-pyridinylamino)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide

HRID 1678418Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:28])[F:27])=[O:17])[CH2:12][CH2:11]2)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:39][C:40]1[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=1>C(#N)C>[CH3:9][NH:8][C:6]1[N:7]=[C:2]([NH:39][C:40]2[CH:45]=[CH:44][N:43]=[CH:42][CH:41]=2)[N:3]=[C:4]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([F:29])([F:27])[F:28])=[O:17])[CH2:14][CH2:15]2)[N:5]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-N-{[2-(trifluoromethyl)phenyl]methyl}-4-piperidinecarboxamide (75 mg, 0.18 mmol, 1.0 equiv) and diisopropylethylamine (DIEA, 154 □l, 0.875 mmol, 5.00 equiv) in acetonitrile (3 ml) at room temperature, 4-aminopyridine (43.0 mg, 0.349 mmol, 2.00 equiv) was added. The reaction mixture was heated to 65° C. and stirring was continued overnight. The reaction mixture was cooled to room temperature, and the solvent was removed under reduced pressure. The residue was dissolved up in 1.5 ml DMSO and purified via reverse-phase HPLC purification to afford the title compound. MS (ES+): m/e 487.1 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was removed under reduced pressure
dissolutionThe residue was dissolved up in 1.5 ml DMSO
custompurified via reverse-phase HPLC purification

Sources & evidence

ORD record: ord-5e4f660916e04a2c9e4fe7a908b4b0ab
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08008483B2

Reaction notes

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