Triethylamine → 1-(4-{7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-3-(3-trifluoromethyl-phenyl)-urea

HRID 1446750Notes

Reaction equation

HRID 1446750 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=5)=[CH:21][N:22]=[C:16]4[CH:15]=3)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[F:30][C:31]([F:42])([F:41])[C:32]1[CH:33]=[C:34]([N:38]=[C:39]=[O:40])[CH:35]=[CH:36][CH:37]=1.C(N(CC)CC)C>CS(C)=O>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[N:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][N:17]4[C:20]([C:23]5[CH:28]=[CH:27][C:26]([NH:29][C:39]([NH:38][C:34]6[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([F:30])([F:41])[F:42])[CH:33]=6)=[O:40])=[CH:25][CH:24]=5)=[CH:21][N:22]=[C:16]4[CH:15]=3)=[CH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 685432324-{7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenylamine

Product 1

HCID 578634351-(4-{7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-3-(3-trifluoromethyl-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine the amine (0.164 g, 0.425 mmol), 3-trifluoromethylphenyl isocyanate (0.060 mL, 0.425 mmol) and triethylamine (0.119 mL, 0.851 mmol) in DMSO (5 mL). Stir the mixture at room temperature for ninety minutes. Extract the mixture with ethyl acetate versus water. Wash the organic layer with saturated aqueous saturated sodium chloride. Dry the resulting organics over magnesium sulfate, filter, and concentrate. Purify by column chromatography (ethyl acetate→5% methanol in dichloromethane→10% methanol in dichloromethane) to afford product (0.056 g, 13%, two steps). MS(ES), m/z 573 (M+1).

Workup

  1. extractionExtract the mixture with ethyl acetate versus water
  2. washWash the organic layer with saturated aqueous saturated sodium chloride
  3. dry with materialDry the resulting organics over magnesium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by column chromatography (ethyl acetate→5% methanol in dichloromethane→10% methanol in dichloromethane)
  7. customto afford product (0.056 g, 13%, two steps)

Sources & evidence

ORD record
ord-f16ec516eaf64dfbb5556bc9bf0732d4
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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