Potassium Carbonate → (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester

HRID 550838Notes

Reaction equation

HRID 550838 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[C:11]2[N:18]=[C:17]([NH:19][C:20]([N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)=[O:21])[S:16][C:12]=2[N:13]=[CH:14][N:15]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])[O-].[K+].[K+].[CH3:43][O:44][C:45](=[O:55])[CH:46](Br)[C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=1>CN(C)C=O.CO>[CH3:43][O:44][C:45](=[O:55])[CH:46]([C:47]1[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=1)[N:25]1[CH2:24][CH2:23][N:22]([C:20](=[O:21])[NH:19][C:17]2[S:16][C:12]3[N:13]=[CH:14][N:15]=[C:10]([O:9][CH3:8])[C:11]=3[N:18]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 19385736Methyl 2-bromo-2-(3-chlorophenyl)acetateHCID 86616508Piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide trifluoroacetate salt

Product 1

HCID 24830454(3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Piperazine-1-carboxylic acid (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-amide trifluoroacetate salt (1.56 g, 3.82 mmol), diisopropylethylamine (2.7 mL, 15.5 mmol) in N,N-dimethylformamide (15 mL) was stirred at room temperature for 30 minutes. To the mixture was added potassium carbonate (0.8 g, 5.8 mmole) and Bromo-(3-chloro-phenyl)-acetic acid methyl ester (1.0 g, 3.8 mmol) and the resulting mixture was stirred at room temperature overnight. Filtration and concentration gave a solid which was dissolved in methanol and absorbed onto 2 g of silica gel. The silica gel was loaded onto an Isco 120 g column and eluted using 0→5% Methanol/methylene chloride to yield (3-Chloro-phenyl)-[4-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-piperazin-1-yl]-acetic acid methyl ester as a white powder; LRMS for C20H21ClN6O4S (M+H)+ at m/z=477. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. filtrationFiltration and concentration
  3. customgave a solid which
  4. customabsorbed onto 2 g of silica gel
  5. washeluted

Sources & evidence

ORD record
ord-d3e7063a53e24dacbd8887e1d216fba1
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

Loading…