Piperazine → HCID 57863429, compound

HRID 1446742Notes

Reaction equation

HRID 1446742 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][N:16]4[C:19]([C:22]5[CH:42]=[CH:41][C:25]([CH2:26][NH:27][C:28]([NH:30][C:31]6[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=6)=[O:29])=[CH:24][CH:23]=5)=[CH:20][N:21]=[C:15]4[CH:14]=3)=[CH:9][CH:8]=2)CCOC[CH2:2]1.C([O-])([O-])=O.[K+].[K+].N1CCNCC1>CS(C)=O>[CH3:2][NH:1][C:7]1[N:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]3[C:19]([C:22]4[CH:23]=[CH:24][C:25]([CH2:26][NH:27][C:28]([NH:30][C:31]5[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:38])[F:39])[CH:32]=5)=[O:29])=[CH:41][CH:42]=4)=[CH:20][N:21]=[C:15]3[CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 68544802HCID 68544802, compound

Product 1

HCID 57863429HCID 57863429, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

Dissolve 1-{4-[7-(6-Morpholin-4-yl-pyridin-3-yl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-3-(3-trifluoromethyl-phenyl)-urea (0.220 g, 0.435 mmol, 1.0 eq.) in DMSO (2 mL). Add K2CO3 (0.120 g, 0.870 mmol, 2.0 eq.). Add piperazine (0.150 g, 1.74 mmol, 4.0 eq.). Stir the reaction mixture at 80° C. overnight under nitrogen. Pour the reaction mixture into 40 mL of ice and filter. Purify the yellow solid by silica gel chromatography using a 0-5% MeOH/DCM gradient to give the title compound 0.170 g (0.33 mmol, 76%) as a slightly yellow solid: MS(ES), m/z 518 (M+1).

Workup

  1. filtrationfilter
  2. customPurify the yellow solid by silica gel chromatography

Sources & evidence

ORD record
ord-ccbefbc843834c4c8cc054c1b3f39be4
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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