Piperidine → HCID 9968042, 화합물

HRID 1828563노트

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HRID 1828563 반응식
[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

참가 물질

9

반응물 5

HCID 8082PiperidineHCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 22066062HCID 22066062, 화합물

생성물 2

HCID 9968042HCID 9968042, 화합물HCID 10155451HCID 10155451, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-aebc1b1aa1984c5589c294f7bc3adf94
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07057051B2

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