Morpholine → 1-[5-tert-Butyl-2-(2-morpholin-4-yl-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea

HRID 1446734Notes

Reaction equation

HRID 1446734 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:17][CH:16]=2)=[O:12])[N:7]([CH2:40][CH2:41]OS(C)(=O)=O)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:47]1[CH2:52][CH2:51][O:50][CH2:49][CH2:48]1.CCOC(C)=O>CN(C=O)C>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:25]4[CH:26]=[CH:27][C:28]([C:30]5[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:37])=[O:38])=[CH:32][CH:31]=5)=[CH:29][C:24]4=[N:23][CH:22]=3)=[CH:19][CH:20]=2)=[O:12])[N:7]([CH2:40][CH2:41][N:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8857Ethyl AcetateHCID 86634307Methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl ester

Product 1

HCID 578634231-[5-tert-Butyl-2-(2-morpholin-4-yl-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureaYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round bottomed flask, dissolve methanesulfonic acid 2-[3-tert-butyl-5-(3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureido)-pyrazol-1-yl]-ethyl ester (75 mg, 0.11 mmol) in DMF (2 mL). Add morpholine (0.1 mL, 10 eq) and heat the reaction to 70° C. overnight under N2. Dilute the reaction with EtOAc then wash with water, 1 N NaOH, and saturated aqueous saturated sodium chloride. Dry the organics over magnesium sulfate, filter, and concentrate. Purify the compound on a silica gel column (EtOAc to 5% MeOH: DCM to 10% 2 M NH3 in MeOH: DCM) to give a pale yellow solid (46 mg, 62%). MS (ES), m/z 656 (M+1).

Workup

  1. customthe reaction to 70° C. overnight under N2
  2. additionDilute
  3. washthen wash with water, 1 N NaOH, and saturated aqueous saturated sodium chloride
  4. dry with materialDry the organics over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the compound on a silica gel column (EtOAc to 5% MeOH: DCM to 10% 2 M NH3 in MeOH: DCM)

Sources & evidence

ORD record
ord-302f09a3f6e04ce3adc33357873e10dc
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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