1-(2-Hydroxyethyl)piperazine → HCID 86625643, compound

HRID 1442441Notes

Reaction equation

HRID 1442441 reaction equation
[C:1]([C:4]([NH:7][C:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[C:22]([O:29][C@@H:30]3[O:56][C@H:55]([CH2:57][O:58][C:59](=[O:64])[C:60]([CH3:63])([CH3:62])[CH3:61])[C@@H:47]([O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]3[O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[N:23][NH:24][C:25]=2[CH:26]([CH3:28])[CH3:27])=[C:16]([CH3:65])[CH:15]=1)=[O:9])([CH3:6])[CH3:5])(O)=[O:2].[OH:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][NH:72][CH2:71][CH2:70]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C)C=O.O.C(N(CC)CC)C>[OH:66][CH2:67][CH2:68][N:69]1[CH2:74][CH2:73][N:72]([C:1]([C:4]([NH:7][C:8]([CH2:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]3[C:22]([O:29][C@@H:30]4[O:56][C@H:55]([CH2:57][O:58][C:59](=[O:64])[C:60]([CH3:63])([CH3:62])[CH3:61])[C@@H:47]([O:48][C:49](=[O:54])[C:50]([CH3:53])([CH3:52])[CH3:51])[C@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C@H:31]4[O:32][C:33](=[O:38])[C:34]([CH3:35])([CH3:36])[CH3:37])=[N:23][NH:24][C:25]=3[CH:26]([CH3:27])[CH3:28])=[C:16]([CH3:65])[CH:15]=2)=[O:9])([CH3:5])[CH3:6])=[O:2])[CH2:71][CH2:70]1

Participants

8

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86606852HCID 86606852, compound

Product 1

HCID 86625643HCID 86625643, compoundYield 60.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[(4-{3-[1-carboxy-1-(methyl)ethyl-carbamoyl]propoxy}-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (40 mg) in N,N-dimethylformamide (2 mL) were added 1-(2-hydroxyethyl)piperazine (7 mg), 1-hydroxybenzotriazole (7 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (13 mg) and triethylamine (0.018 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=15/1) to give 4-[(4-{3-[1-{[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}-1-(methyl)ethyl-carbamoyl]propoxy}-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (27 mg). This material was dissolved in methanol (2 mL). To the solution was added sodium methoxide (28% methanol solution, 0.015 mL), and the mixture was stirred at 50° C. overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (12 mg).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: dichloro-methane/methanol=15/1)

Sources & evidence

ORD record
ord-7b8b271c66d244438151900b69dccfb1
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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