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

HRID 1446752Notes

Reaction equation

HRID 1446752 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.ClC(Cl)(Cl)C[O:33][C:34](=O)[NH:35][C:36]1[CH:40]=[C:39]([C:41]([CH3:44])([CH3:43])[CH3:42])[O:38][N:37]=1.C(N(CC)CC)C>CS(C)=O>[C:41]([C:39]1[O:38][N:37]=[C:36]([NH:35][C:34]([NH:29][C:26]2[CH:27]=[CH:28][C:23]([C:20]3[N:17]4[CH:18]=[CH:19][C:14]([C:11]5[CH:12]=[N:13][C:8]([N:5]6[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]6)=[N:9][CH:10]=5)=[CH:15][C:16]4=[N:22][CH:21]=3)=[CH:24][CH:25]=2)=[O:33])[CH:40]=1)([CH3:44])([CH3:42])[CH3:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22768171HCID 22768171, compoundHCID 685432324-{7-[2-(4-Methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenylamine

Product 1

HCID 578634401-(5-tert-Butyl-isoxazol-3-yl)-3-(4-{7-[2-(4-methyl-piperazin-1-yl)-pyrimidin-5-yl]-imidazo[1,2-a]pyridin-3-yl}-phenyl)-urea

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

Combine the amine (0.323 g, 0.838 mmol), (5-tert-butyl-isoxazol-3-yl)-carbamic acid 2,2,2-trichloro-ethyl ester (0.291 g, 0.922 mmol) and triethylamine (0.128 mL, 0.922 mmol) in DMSO (10 mL). Heat the mixture to 70° C., stir overnight, and cool to room temperature. 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→10% methanol in dichloromethane→10% 2 M NH3 in MeOH in dichloromethane) to afford product (0.057 g, 11%, two steps). MS(ES), m/z 552 (M+1).

Workup

  1. temperaturecool to room temperature
  2. extractionExtract the mixture with ethyl acetate versus water
  3. washWash the organic layer with saturated aqueous saturated sodium chloride
  4. dry with materialDry the resulting organics over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by column chromatography (ethyl acetate→10% methanol in dichloromethane→10% 2 M NH3 in MeOH in dichloromethane)
  8. customto afford product (0.057 g, 11%, two steps)

Sources & evidence

ORD record
ord-1b5b4bcb03c1466d95010c85d4705b23
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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