Potassium Carbonate → HCID 49763995, compound

HRID 2365619Notes

Reaction equation

HRID 2365619 reaction equation
[C:1]1([C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:18][N:17]([C:19]([C:21]4[CH:22]=[C:23]5[C:28](=[CH:29][CH:30]=4)[CH2:27][NH:26][CH2:25][CH2:24]5)=[O:20])[CH2:16]3)[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:7]([N:26]1[CH2:25][CH2:24][C:23]2[C:28](=[CH:29][CH:30]=[C:21]([C:19]([N:17]3[CH2:16][CH:15]([N:12]4[CH2:11][CH2:10][N:9]([C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[O:8])[CH2:14][CH2:13]4)[CH2:18]3)=[O:20])[CH:22]=2)[CH2:27]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 59625903HCID 59625903, compound

Product 1

HCID 49763995HCID 49763995, compoundYield 139%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of compound 17a (100 mg) and K2CO3 (69 mg) in MeCN was added compound 18a (0.0353 mL) and the mixture was stirred at room temperature for 30 min. The reaction was concentrated and the residue was diluted with EtOAc and water. The organics were concentrated and purified by flash column chromatography (silica gel, 8% MeOH/EtOAc) to afford compound 355 (85 mg). MS m/z (M+H+) 495.6.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with EtOAc and water
  3. concentrationThe organics were concentrated
  4. custompurified by flash column chromatography (silica gel, 8% MeOH/EtOAc)

Sources & evidence

ORD record
ord-e63f0efd18a74141bb0f03cbb92a4c9d
Source dataset
uspto-grants-2014_04
Patent number
US08697683B2

Reaction notes

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