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

HRID 1446732Notes

Reaction equation

HRID 1446732 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[N:35]4[CH:36]=[CH:37][C:38]([C:40]5[CH:45]=[CH:44][C:43]([S:46]([CH3:49])(=[O:48])=[O:47])=[CH:42][CH:41]=5)=[CH:39][C:34]4=[N:33][CH:32]=3)=[CH:27][CH:26]=2)=[O:22])[N:8]([CH2:10][CH2:11][O:12][Si](C(C)(C)C)(C)C)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([C:5]1[CH:6]=[C:7]([NH:20][C:21]([NH:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]3[N:35]4[CH:36]=[CH:37][C:38]([C:40]5[CH:41]=[CH:42][C:43]([S:46]([CH3:49])(=[O:47])=[O:48])=[CH:44][CH:45]=5)=[CH:39][C:34]4=[N:33][CH:32]=3)=[CH:29][CH:30]=2)=[O:22])[N:8]([CH2:10][CH2:11][OH:12])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 685449601-{5-tert-Butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-yl}-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea

Product 1

HCID 578634381-[5-tert-Butyl-2-(2-hydroxy-ethyl)-2H-pyrazol-3-yl]-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-ureaYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a round bottomed flask dissolve 1-{5-tert-butyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2H-pyrazol-3-yl}-3-{4-[7-(4-methanesulfonyl-phenyl)-imidazo[1,2-a]pyridin-3-yl]-benzyl}-urea (0.26 g, 0.37 mmol) in THF (5 mL) under N2, Add TBAF (0.41 mL of a 1M solution in THF, 1.1 equiv.) via syringe and stir the reaction at room temperature for 20 minutes. Load the reaction directly onto a silica column and purify (EtOAc to 5% MeOH: DCM to 10% 2 M NH3 in MeOH: DCM) to give a pale yellow solid (0.168 g, 77%). MS (ES), m/z 587 (M+1).

Workup

  1. customthe reaction at room temperature for 20 minutes
  2. customLoad the reaction directly onto a silica column
  3. custompurify (EtOAc to 5% MeOH: DCM to 10% 2 M NH3 in MeOH: DCM)

Sources & evidence

ORD record
ord-2569d8e6f39648c6aec6f5545394deca
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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