Ethanol → HCID 86664798, compound

HRID 2047230Notes

Reaction equation

HRID 2047230 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([C:23]2[CH:28]=[C:27]([N:29]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[N:26]3[N:46]=[CH:47][C:48]([C:49]4[CH:50]=[N:51][C:52]5[C:57]([CH:58]=4)=[CH:56][C:55]([F:59])=[CH:54][CH:53]=5)=[C:25]3[N:24]=2)[C:16](=[O:22])[O:17][C:18]([CH3:21])(C)C)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+].[CH2:64](O)[CH3:65]>[OH-].[OH-].[Pd+2]>[CH3:35][Si:34]([CH3:36])([CH3:37])[CH2:33][CH2:32][O:31][CH2:30][N:29]([CH2:38][O:39][CH2:40][CH2:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:27]1[N:26]2[N:46]=[CH:47][C:48]([C:49]3[CH:50]=[N:51][C:52]4[C:57]([CH:58]=3)=[CH:56][C:55]([F:59])=[CH:54][CH:53]=4)=[C:25]2[N:24]=[C:23]([N:15]([CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[C:16](=[O:22])[O:17][CH2:18][CH2:21][CH2:64][CH3:65])[CH:28]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 86664797HCID 86664797, compound

Product 1

HCID 86664798HCID 86664798, compound

Reagents, catalysts & solvents 1

HCID 9942167Palladium hydroxideCatalyst

Procedure

This material, tert-butyl (1-benzylpiperidin-4-yl)methyl(7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)carbamate, was then stirred with Pd(OH)2/C (0.2 equiv) and ammonium formate (20 equiv) in ethanol at 80° C. until the reaction was deemed complete by HPLC, LC-MS, or TLC analysis. The mixture was allowed to cool to room temperature, filtered through a pad of celite, concentrated and purified on silica gel to afford compound tea-butyl 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl(piperidin-4-ylmethyl)carbamate.

Workup

  1. filtrationfiltered through a pad of celite,
  2. concentrationconcentrated
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-b627ed6af6864384a0c9cccb9e09f7bd
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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