Potassium Carbonate → HCID 68496157, compound

HRID 1038755Notes

Reaction equation

HRID 1038755 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:12]([OH:14])=O)[N:8]2[CH3:11])=[CH:4][CH:3]=1.[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1.Cl[C:52]1[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][N:53]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:15]([O:19][C:20]([N:22]1[CH2:27][CH2:26][N:25]([C:12]([C:7]2[N:8]([CH3:11])[C:9]3[C:5]([CH:6]=2)=[CH:4][CH:3]=[C:2]([O:1][C:52]2[CH:57]=[CH:56][C:55]([N+:58]([O-:60])=[O:59])=[CH:54][N:53]=2)[CH:10]=3)=[O:14])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

8

Reactant 6

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23510098HCID 23510098, compound

Product 1

HCID 68496157HCID 68496157, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 6-hydroxy-1-methyl-1H-indole-2-carboxylic acid (12.27 g, 64.2 mmol) and piperazine-1-carboxylic acid tert-butyl ester (14.34 g, 77.0 mmol) in DMF (80 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (18.4 g, 96.0 mmol) and 1-hydroxybenzotriazole monohydrate (11.6 g, 75.7 mmol) under ice cooling, and the mixture was stirred at room temperature overnight. The mixture was evaporated under reduced pressure, and then water and AcOEt were added to the residue. The organic layer was separated and washed with 1M HCl, saturated aqueous NaHCO3 and brine, dried over anhydrous magnesium sulfate and evaporated. To a mixture of the residue and 2-chloro-5-nitropyridine (10.05 g, 63.4 mmol) in DMF (80 mL) was added K2CO3 (11.92 g, 86.2 mmol) and the mixture was stirred overnight at room temperature. The mixture was evaporated under reduced pressure, and then water and Et2O were added to the residual mixture. After the mixture was stirred for 1 hour, the precipitate was collected by filtration and dried to afford 23.2 g of the title compound as a yellow powder.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. additionwater and AcOEt were added to the residue
  3. customThe organic layer was separated
  4. washwashed with 1M HCl, saturated aqueous NaHCO3 and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. stirringthe mixture was stirred overnight at room temperature
  8. customThe mixture was evaporated under reduced pressure
  9. additionwater and Et2O were added to the residual mixture
  10. stirringAfter the mixture was stirred for 1 hour
  11. filtrationthe precipitate was collected by filtration
  12. customdried

Sources & evidence

ORD record
ord-1cead2abede142cfab586fc9574b2d27
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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