Piperidine → HCID 9968042、化合物

HRID 1828563ノート

反応式

HRID 1828563 の反応式
[C:1]1([C:7]2[N:8]=[C:9]([C:19](O)=[O:20])[N:10]([CH3:18])[C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl.O>[N:23]1([NH:22][C:19]([C:9]2[N:10]([CH3:18])[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[O:20])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[N:29]1([C:19]([C:9]2[N:10]([CH3:18])[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:8]=2)=[O:20])[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

参加物

9

反応物 5

HCID 8082PiperidineHCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 22066062HCID 22066062、化合物

生成物 2

HCID 9968042HCID 9968042、化合物HCID 10155451HCID 10155451、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4,5-diphenyl-I-methylimidazole-2-carboxylic acid (50 mg, 0.18 mmol) from Step A, 1-aminopiperidine (0.052 mL, 0.36 mmol) (containing a small percent of piperidine as an impurity), PyBOP (NovaChem) (140 mg, 0.2 mmol) and N,N-diisopropyl-N-ethylamine (DIPEA) (0.065 mL, 0.2 mmol) in methylene chloride (2 mL) was stirred at rt for 20 hr. The reaction was diluted with water and extracted twice with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified twice by prep TLC (1 mm, silica gel) eluting with 5% methylene chloride, 35% ethyl acetate in hexanes to afford the primary product N-(piperidin-1-yl)-4,5-diphenyl-1-methylimidazole-2-carboxamide and 2-(piperidin-1-ylcarbonyl)-4,5-diphenyl-1-methylimidazole as a byproduct. HPLC/MS: 361 (M+1); Rt=2.64 min; 1HNMR (CDCl3): 1.4–1.7 (m, 2H), 1.92 (m, 4H), 2.96 (br s, 4H), 3.90 (s, 3H), 7.24 (m, 3H), 7.34 (m, 2H), 7.50 (m, 5H).

後処理

  1. extractionextracted twice with methylene chloride
  2. washThe organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified twice by prep TLC (1 mm, silica gel)
  6. washeluting with 5% methylene chloride, 35% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-aebc1b1aa1984c5589c294f7bc3adf94
出典データセット
uspto-grants-2006_06
特許番号
US07057051B2

反応ノート

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