Methanol → HCID 44192428, compound

HRID 1677411Notes

Reaction equation

HRID 1677411 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][C:15]3=[O:24])[N:12]=2)[N:7](COCC[Si](C)(C)C)[CH:6]=1)=[O:4].O.O.O.C([O-])(=O)C.[Na+].CO.[Cl:45][CH2:46][Cl:47]>FC(F)(F)C(O)=O>[NH4+:7].[OH-:4].[Cl:45][CH2:46][Cl:47].[CH3:1][C:2]([CH3:34])([CH3:33])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH2:17][CH2:16][C:15]3=[O:24])[N:12]=2)[NH:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 6344Dichloromethane2×HCID 23665404Sodium Acetate TrihydrateHCID 67203355HCID 67203355, compound

Product 2

HCID 21919329HCID 21919329, compoundHCID 44192428HCID 44192428, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-3,4-dihydro-1H-quinolin-2-one (0.2562 g, 0.535 mmol) in 2 mL of dichloromethane and 2 mL of trifluoroacetic acid was stirred for 5 h then concentrated to a yellow oil. The oil was dissolved in 2 mL of ethanol and the solution was treated with sodium acetate trihydrate (01.3 g, 9.55 mmol). Silica gel chromatography (0→50% 60:10:1 CH2Cl2:MeOH:NH4OH/dichloromethane) afforded 0.1626 g (87% yield) of 1-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-3,4-dihydro-1H-quinolin-2-one as a yellow solid.

Workup

  1. concentrationthen concentrated to a yellow oil
  2. dissolutionThe oil was dissolved in 2 mL of ethanol

Sources & evidence

ORD record
ord-a5af54ec4cc24d4e9eadb513f6f81ab7
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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