Nicotinic Acid → HCID 10114635, compound

HRID 1374145Notes

Reaction equation

HRID 1374145 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]3=[O:25])[CH2:12][CH2:11]2)[CH3:9])[CH2:3][CH2:2]1.[C:26](O)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[OH-].[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]([N:10]3[CH2:15][CH2:14][CH:13]([N:16]4[C:20]5[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=5[NH:18][C:17]4=[O:25])[CH2:12][CH2:11]3)[CH3:9])[CH2:3][CH2:2]2)=[O:33])[CH:28]=1

Participants

8

Reactant 5

HCID 938Nicotinic AcidHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21076286HCID 21076286, compound

Product 1

HCID 10114635HCID 10114635, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Procedure

To 9.7 mg of 1-[1-[2-(piperidin-4-yl)-1-methylethyl]-piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one which was synthesized by the method of Production Example 6, 1 ml of chloroform, 4.4 mg of nicotinic acid, 8 mg of 1-ethyl-3-[3-(dimethylamino)propyl]-carbodiimide hydrochloride, 6.4 mg of 1-hydroxybenzotriazole and 0.01 ml of triethylamine were added and stirred for an overnight. To the reaction liquid 1N aqueous sodium hydroxide solution and chloroform were added to separate the reaction liquid. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off, and the residue was purified on silica gel chromatography (chloroform/methanol=11:1) to provide 10.1 mg of the title compound as a colorless solid.

Workup

  1. additionwere added
  2. additionwere added
  3. customto separate
  4. customthe reaction liquid
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified on silica gel chromatography (chloroform/methanol=11:1)

Sources & evidence

ORD record
ord-e9944b9f8c5c489db1efb82de106c05a
Source dataset
uspto-grants-2007_01
Patent number
US07164024B2

Reaction notes

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