Acetone → HCID 46900750, compound

HRID 1749068Notes

Reaction equation

HRID 1749068 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[C:24](OCC)(=O)[CH:25]=[O:26].CC(C)=O>C(O)C.C1(C)C=CC=CC=1>[O:26]=[C:25]1[CH:24]=[N:1][C:2]2[N:3]=[CH:4][CH:5]=[C:6]([O:9][C:10]3[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[CH:14][CH:15]=3)[C:7]=2[NH:8]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 70211Ethyl oxoacetateHCID 42625416Tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate

Product 1

HCID 46900750HCID 46900750, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

tert-butyl 4-(2,3-diaminopyridin-4-yloxy)phenylcarbamate (0.86 g, 2.71 mmol) was dissolved in 15 ml of dry ethanol; 0.8 ml (4 mmol) of a 50% ethyl glyoxalate solution in toluene were added and the solution was stirred overnight at room temperature under Argon atmosphere. The solvent was partially evaporated, and tert-butyl 4-(2-oxo-1,2-dihydropyrido[2,3-b]pyrazin-8-yloxy)phenylcarbamate (0.430 g, 45% yield) is precipitated by addition of acetone (10 ml) and filtered off.

Workup

  1. customThe solvent was partially evaporated

Sources & evidence

ORD record
ord-5f7a0fd6e2dc4aa1a7b1ea0446fc204e
Source dataset
uspto-grants-2015_10
Patent number
US09155737B2

Reaction notes

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