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Potassium Carbonate → tert-Butyl [(5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetate

HRID 534900
Notes
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Reaction equation

HRID 534900 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[OH:19][C:20]1[CH:21]=[C:22]([C:26]([OH:28])=O)[CH:23]=[N:24][CH:25]=1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.Br[CH2:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55].C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O.C(N(CC)CC)C>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:26]([C:22]2[CH:21]=[C:20]([O:19][CH2:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH:25]=[N:24][CH:23]=2)=[O:28])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 11430Potassium CarbonateHCID 340375-Hydroxynicotinic acidHCID 79177tert-Butyl bromoacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667511491-(2-Tert-butylphenyl)piperazine dihydrochloride

Product 1

HCID 66751333tert-Butyl [(5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyridin-3-yl)oxy]acetateYield 68%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)piperazine dihydrochloride obtained in Reference Example 1 (500 mg), 5-hydroxypyridine-3-carboxylic acid (287 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (403 mg), 1-hydroxy-1H-benzotriazole monohydrate (322 mg), triethylamine (0.488 mL), and N,N-dimethylformamide (5 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide a powder (LC/MS (ESI+) m/z: 340 (M+H)+). A mixture of the powder, tert-butyl bromoacetate (683 mg), potassium carbonate (691 mg), and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 5 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate) to provide the title compound (530 mg, 68%) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customto provide a powder (LC/MS (ESI+) m/z: 340 (M+H)+)
  6. stirringwas stirred at 60° C. for 5 h
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. customthe residue was purified by flash column chromatography (silica gel, 90:10-50:50 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1592e319a7094da195ccc565a1fcb5eb
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853215B2

Reaction notes

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