Thiophene-3-carboxylic acid → HCID 58978020, compound

HRID 1179328Notes

Reaction equation

HRID 1179328 reaction equation
[CH:1]1[S:5][CH:4]=[CH:3][C:2]=1[C:6]([OH:8])=O.Cl.Cl.[NH:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]3=[O:32])[CH2:19][CH2:18]2)[CH2:13][CH2:12]1.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.C(O)(C)(C)C.C(N(CC)CC)C>[CH:1]1[S:5][CH:4]=[CH:3][C:2]=1[C:6]([N:11]1[CH2:12][CH2:13][CH:14]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]3=[O:32])[CH2:21][CH2:22]2)[CH2:15][CH2:16]1)=[O:8]

Participants

9

Reactant 5

HCID 6918Thiophene-3-carboxylic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 227452031-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride

Product 1

HCID 58978020HCID 58978020, compoundYield 87.5%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6386tert-ButanolSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 72 mg of 3-thenoic acid, 187 mg of 1-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride, 110 mg of ethyl 3-(dimethylamino)propylcarbodiimide, 110 mg of 1-hydroxy-1,2,3-benzotriazole, 300 mg of triethylamine, 10 ml of CHCl3, and 10 ml of tert-butyl alcohol was stirred for 17 h. The reaction mixture was partitionized between chloroform and aqueous NaHCO3. The organic layer was washed with aqueous NaHCO3, dried over anhydrous Na2SO4, and concentrated. The residue was purified on SiO2 chromatography (chloroform/methanol=30:1-20:1) to afford 180 mg of 1-[1-[1-(3-thenoyl)piperidin-4-yl]piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one as a colorless amorphous.

Workup

  1. washThe organic layer was washed with aqueous NaHCO3
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified on SiO2 chromatography (chloroform/methanol=30:1-20:1)

Sources & evidence

ORD record
ord-87a1fb708dfe4bbc848b9853beabade0
Source dataset
uspto-grants-2007_10
Patent number
US07279490B2

Reaction notes

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