Potassium Carbonate → HCID 60090595, compound

HRID 852302Notes

Reaction equation

HRID 852302 reaction equation
[OH:1][CH2:2][CH:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18](=O)[C:19]([CH3:24])=[CH:20]N(C)C)[CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:26]1([NH:29][C:30]([NH2:32])=[NH:31])[CH2:28][CH2:27]1.Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.C(OCC)(=O)C>[OH:1][CH2:2][C@@H:3]([NH:10][C:11]([C:13]1[NH:14][CH:15]=[C:16]([C:18]2[C:19]([CH3:24])=[CH:20][N:32]=[C:30]([NH:29][CH:26]3[CH2:28][CH2:27]3)[N:31]=2)[CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 73701889HCID 73701889, compoundHCID 178479365HCID 178479365, compound

Product 1

HCID 60090595HCID 60090595, compoundYield 7.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

4-(3-Dimethylamino-2-methyl-acryloyl)-1H-pyrrole-2-carboxylic acid (2-hydroxy-1-phenyl-ethyl)-amide (100 mg, 0.29 mmol) was combined with cyclopropyl guanidine•HCl (80 mg) and potassium carbonate (121 mg) in N,N-dimethylacetamide (2 mL). The resulting suspension was heated and stirred at 100° C. for 24 hours. The crude material was diluted with ethyl acetate, washed with saturated NaHCO3 and brine, dried over MgSO4 then concentrated in vacuo. Purification by preparative TLC (silica, 1:1 EtOAc:Hexanes) afforded III-a-162 as a yellow solid (7.8 mg). HPLC Method B, Rt=4.29 minutes; LC/MS(m/z) 378.2 (M+1), 376.2 (M−1); 1H NMR consistent with structure.

Workup

  1. temperatureThe resulting suspension was heated
  2. washwashed with saturated NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationthen concentrated in vacuo
  5. customPurification by preparative TLC (silica, 1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-2de8d9a8ffbe4fd88130759f4fd53cc2
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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