4-Methylpiperidin-4-ol → 1-(2-((6-Chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)-4-methylpiperidin-4-ol

HRID 455108Notes

Reaction equation

HRID 455108 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:9][C:10]2[N:14]3[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]3=[N:12][C:11]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:3]=1.[CH3:26][C:27]1([OH:33])[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>CC(O)(C)C.C(OCC)(=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]2[N:14]([C:10]([CH2:9][NH:8][C:4]3[N:3]=[C:2]([N:30]4[CH2:31][CH2:32][C:27]([CH3:26])([OH:33])[CH2:28][CH2:29]4)[CH:7]=[CH:6][N:5]=3)=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:12]=2)[CH:15]=1

Participants

5

Reactant 2

HCID 156491744-Methylpiperidin-4-olHCID 866551254-chloro-N-((6-chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-2-amine

Product 1

HCID 670290991-(2-((6-Chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methylamino)pyrimidin-4-yl)-4-methylpiperidin-4-ol

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 4-chloro-N-((6-chloro-2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)pyrimidin-2-amine (50 mg, 0.135 mmol) and 4-methylpiperidin-4-ol (200 mg, 1.74 mmol) in t-BuOH (0.5 ml) was heated 95° C. until the reaction was completed. The mixture was diluted with ethyl acetate and the resulting mixture was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated by evaporation. The crude product was purified by silica gel chromatography (methanol/methylene chloride gradient) to title compound. M/e+ 449 for C24H26ClN6O (M+H)+; 1H-NMR (400 MHz, CDCl3) δ 8.47 (s, 1H), 7.89 (d, J=5.8 Hz, 1H), 7.76 (d, J=6.9 Hz, 2H), 7.57 (d, J=9.5 Hz, 1H), 7.47 (m, 3H), 7.39 (d, J=7.7 Hz, 1H), 7.16 (dd, J=9.5, 1.8 Hz, 1H), 5.99 (d, J=6.2 Hz, 1H), 5.05 (d, J=5.5 Hz, 2H), 5.00 (bs, 1H), 4.00 (m, 2H), 3.40 (m, 2H), 1.62 (m, 4H), 1.29 (s, 3H) ppm.

Workup

  1. washthe resulting mixture was washed with saturated NaHCO3 and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by evaporation
  4. customThe crude product was purified by silica gel chromatography (methanol/methylene chloride gradient) to title compound

Sources & evidence

ORD record
ord-f31b6bbf35ad410fb51038b77f869e64
Source dataset
uspto-grants-2013_07
Patent number
US08497278B2

Reaction notes

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