2-Pyrazinecarboxylic acid → HCID 10137795, compound

HRID 1374140Notes

Reaction equation

HRID 1374140 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:5][CH2:4]1.[N:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[C:33](O)=[O:34].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>[N:27]1[CH:32]=[CH:31][N:30]=[CH:29][C:28]=1[C:33]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:5][CH2:4]1)=[O:34]

Participants

9

Reactant 5

HCID 10472-Pyrazinecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21076287HCID 21076287, compound

Product 1

HCID 10137795HCID 10137795, compoundYield 50.6%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 73 mg of 1-[1-[2-(piperidin-4-yl)ethyl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride which was synthesized in Production Example 1, 28 mg of pyrazinecarboxylic acid, 101 μl of triethylamine and 14 mg of 1-hydroxybenzotriazole were added, and the mixture was suspended in 5 ml of chloroform. Then 52 mg of 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride was added to the suspension, and the resulting reaction mixture was stirred for 3 hours at room temperature. To the reaction liquid, ethyl acetate and saturated aqueous sodium hydrogencarbonate solution were added and mixed by shaking, to recover the separated organic layer. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off. The resulting residue was purified on silica gel chromatography (chloroform/methanol=10/1) to provide 40 mg of the title compound as a colorless oil.

Workup

  1. additionwere added
  2. customthe resulting reaction mixture
  3. additionwere added
  4. additionmixed
  5. stirringby shaking
  6. customto recover the separated organic layer
  7. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customThe resulting residue was purified on silica gel chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-40ed589c753446fab723983785d0d10d
Source dataset
uspto-grants-2007_01
Patent number
US07164024B2

Reaction notes

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