Thiophene-3-carboxylic acid → HCID 58978020、化合物

HRID 1179328ノート

反応式

HRID 1179328 の反応式
[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]

参加物

9

反応物 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

生成物 1

HCID 58978020HCID 58978020、化合物収率 87.5%

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒2 回HCID 6386tert-Butanol溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-87a1fb708dfe4bbc848b9853beabade0
出典データセット
uspto-grants-2007_10
特許番号
US07279490B2

反応ノート

読み込み中…