1,1'-Carbonyldiimidazole → HCID 25221225、化合物

HRID 1642484ノート

反応式

HRID 1642484 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2([CH3:25])[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]2)[CH2:11][CH2:10]1.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27]>C(#N)C>[CH3:25][C:15]1([N:12]2[CH2:13][CH2:14][CH:9]([N:8]3[C@H:3]4[CH2:4][CH2:5][CH2:6][CH2:7][C@@H:2]4[NH:1][C:26]3=[O:27])[CH2:10][CH2:11]2)[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:16]1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 57619822Ethyl 3-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidinyl]-3-methyl-1-pyrrolidinecarboxylate

生成物 1

HCID 25221225HCID 25221225、化合物収率 7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of ethyl 3-[4-[[(1S,2S)-2-aminocyclohexyl]amino]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate (600 mg, 1.70 mmol) in anhydrous acetonitrile (30 mL) was added with 1,1′-carbonyldiimidazole (551.92 mg, 3.40 mmol) and stirred at room temperature for 12 h. The solvent was removed in vacuo; the residue was dissolved in dichloromethane (60 mL), washed with water and brine and dried over anhydrous MgSO4. Concentrated in vacuo and the residue was purified by flash chromatography (dichloromethane/methanol) to afford the title compound as a white solid (45 mg). 1H NMR (CD3OD, 400 MHz): δ 4.15 (q, 2H), 3.62-3.51 (m, 2H), 2.41 (m, 2H), 3.22 (m, 1H), 3.19 (brd, 1H), 2.99 (m, 3H), 2.76 (brs, 1H), 2.45 (m, 3H), 2.01-1.82 (m, 6H), 1.74 (brd, 1H), 1.65 (brd, 1H), 1.45 (m, 4H), 1.25 (t, 3H), 1.12 (s, 3H). MS (M+1): 379.18.

後処理

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in dichloromethane (60 mL)
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationConcentrated in vacuo
  6. customthe residue was purified by flash chromatography (dichloromethane/methanol)

出典と根拠

ORDレコード
ord-56231d6830b242468801ea9b79f482a0
出典データセット
uspto-grants-2012_02
特許番号
US08119661B2

反応ノート

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