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

HRID 1716593ノート

反応式

HRID 1716593 の反応式
[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]

参加物

3

反応物 1

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

生成物 1

HCID 68513365HCID 68513365、化合物収率 173%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9cf12cbf5063438cad0f48c40a1a8c86
出典データセット
uspto-grants-2010_09
特許番号
US07803816B2

反応ノート

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