Methanol → HCID 59540668, compound

HRID 1677417Notes

Reaction equation

HRID 1677417 reaction equation
C([O:5]C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]3[N:21]=[C:22]4[C:28]([C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:27][N:26]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:42])([CH3:41])[CH3:40])[C:23]4=[N:24][CH:25]=3)[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:43]([Cl:45])[Cl:44].CO>FC(F)(F)C(O)C(F)(F)F>[NH4+:8].[OH-:5].[Cl:44][CH2:43][Cl:45].[CH3:31][C:30]([CH3:33])([CH3:32])[C:29]([C:28]1[C:22]2[C:23](=[N:24][CH:25]=[C:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([N:11]4[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[CH:15]=3)[N:21]=2)[N:26]([CH2:35][O:36][CH2:37][CH2:38][Si:39]([CH3:41])([CH3:40])[CH3:42])[CH:27]=1)=[O:34]

Participants

6

Reactant 3

HCID 887MethanolHCID 6344DichloromethaneHCID 67345225HCID 67345225, compound

Product 2

HCID 21919329HCID 21919329, compoundHCID 59540668HCID 59540668, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

A solution of 4-{3-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester (0.1226 g, 0.206 mmol) in 4 mL of hexafluoroisopropanol was stirred at 150° C. for 1 h under microwave irradiation. The reaction mixture was concentrated in vacuo. Silica gel chromatography (0→40% 60:10:1 CH2Cl2:MeOH:NH4OH/dichloromethane over 20 minutes) afforded 0.0704 g (69% yield) of 2,2-Dimethyl-1-[2-(3-piperazin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one as an off-white solid. MS (E/I): 494 (M+H)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b08b7e569ab34923a9ec8c9ff554efc5
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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