Potassium Carbonate → HCID 59341915, compound

HRID 16015

Reaction equation

HRID 16015 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]2=[N:18][C:19]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[CH:20][N:21]=[C:16]2[N:15]=[N:14]1.I[CH2:28][CH2:29][OH:30].C([O-])([O-])=O.[K+].[K+]>CC(N(C)C)=O>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[CH2:12][N:13]1[C:17]2=[N:18][C:19]([C:22]3[CH:26]=[N:25][N:24]([CH2:28][CH2:29][OH:30])[CH:23]=3)=[CH:20][N:21]=[C:16]2[N:15]=[N:14]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12225IodoethanolHCID 593419587-fluoro-6-{[6-(1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline

Product 1

HCID 59341915HCID 59341915, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
120 °C

Procedure

7-fluoro-6-{[6-(1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl]methyl}quinoline (95 mg, 0.274 mmol), 2-iodoethanol (378 mg, 2.198 mmol), K2CO3 (75.8 mg, 0.548 mmol), DMAC 95 ml) were combined and heated in microwave at 120° C. for 4 h. The reaction mixture was concentrated and the resulting residue was purified via flash column chromatography eluted with 0-5% MeOH:CH2Cl2 to give the desired product as a solid (33.9 mg, 31%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe resulting residue was purified via flash column chromatography
  3. washeluted with 0-5% MeOH

Sources & evidence

ORD record
ord-9b102efab8534f47ba98e66153f18e85
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

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