1-(2-Hydroxyethyl)piperazine → HCID 68495023, compound

HRID 21115Notes

Reaction equation

HRID 21115 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([C:20](O)=[O:21])=[CH:16][C:14]=3[CH:15]=2)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:23].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.[OH:46][CH2:47][CH2:48][N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>CN(C=O)C.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]([N:52]4[CH2:53][CH2:54][N:49]([CH2:48][CH2:47][OH:46])[CH2:50][CH2:51]4)=[O:21])=[CH:16][C:14]=3[CH:15]=2)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:23]

Participants

8

Reactant 4

HCID 76771-(2-Hydroxyethyl)piperazineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 68489207HCID 68489207, compound

Product 1

HCID 68495023HCID 68495023, compoundYield 69.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a similar manner to Step 1 of Example 20, Compound 172 (25.0 mg, 0.0727 mmol) was dissolved in DMF (1 mL), and the solution was treated with EDCI (28 mg, 0.15 mmol), HOBT monohydrate (9.8 mg, 0.073 mmol) and 1-(2-hydroxyethyl)piperazine (38 mg, 0.29 mmol). The reaction mixture was added with water and ethyl acetate, and extracted with 1 mol/L hydrochloric acid. The aqueous layer was added with sodium carbonate to adjust the pH to 9 and extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in chloroform, and the solution was added with diisopropylether and stirred for 30 minutes. The solid was collected by filtration, washed with diisopropylether and then dried under reduced pressure to obtain Compound 173 (22.9 mg, yield 69%).

Workup

  1. extractionextracted with 1 mol/L hydrochloric acid
  2. additionThe aqueous layer was added with sodium carbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in chloroform
  8. additionthe solution was added with diisopropylether
  9. filtrationThe solid was collected by filtration
  10. washwashed with diisopropylether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-f29697db62bf44f78b7aea35823b5ee5
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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