1,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate → HCID 68513365, 화합물

HRID 1716593노트

반응식

HRID 1716593 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=2[NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][C:16]=3[N:22]=[C:6]2[O:5][CH2:1][CH3:2])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

3

반응물 1

HCID 588522881,1-Dimethylethyl 4-[(2-amino-4-methylphenyl)amino]-1-piperidinecarboxylate

생성물 1

HCID 68513365HCID 68513365, 화합물수율 173%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

4-(2-Amino-4-methylphenylamino)-piperidine-1-carboxylic acid tert-butyl ester (361 mg, 1.18 mmol) was mixed with tetraethyl carbonate (272 mg, 1.20 eq) in 4 mL of acetic acid. The mixture was stirred at r.t for 4 hrs until all starting material was consumed. The solution was evaporated and the residue was extracted with ethyl acetate and concentrated NaHCO3 solution. The organic layer was dried and solvents were evaporated. The resulting residue was purified on a Biotage flash column chromatography using ethyl acetate and hexanes (1:2 ratio) to give 4-(2-ethoxy-5-methylbenzoimidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester (367 mg, 86%) as an oil. ES-MS showed m/e 360 (M++1). 1H-NMR (CDCl3) δ 7.33 (s, 1H), 7.10 (d, 1H), 6.92 (d, 1H), 4.58 (q, 2H), 4.23-4.33 (m, 3H), 2.83 (t, 2H), 2.41 (s, 3H), 2.25-2.31 (m, 2H), 1.82 (d, 2H), 1.49 (s, 9H), 1.46 (t, 3H).

후처리

  1. customwas consumed
  2. customThe solution was evaporated
  3. extractionthe residue was extracted with ethyl acetate and concentrated NaHCO3 solution
  4. customThe organic layer was dried
  5. customsolvents were evaporated
  6. customThe resulting residue was purified on a Biotage flash column chromatography

출처 및 근거

ORD 기록
ord-9cf12cbf5063438cad0f48c40a1a8c86
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803816B2

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