1-Pyrrolidineethanamine → HCID 10050407、化合物

HRID 1270984ノート

反応式

HRID 1270984 の反応式
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:29])[NH:9][C:10]2([CH:17](C)[C:18]([NH:20][CH2:21][CH2:22][N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[O:19])[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[CH2:11]2)=[CH:3][CH:2]=1.[C:36]1(C2C=CC=CC=2)C=CC(NC(=O)NC(C2C=CC(C)=CC=2)CC(O)=O)=CC=1.N1(CCN)CCCC1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8](=[O:29])[NH:9][C@@H:10]([C:15]2[CH:36]=[CH:11][C:12]([CH3:16])=[CH:13][CH:14]=2)[CH2:17][C:18]([NH:20][CH2:21][CH2:22][N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:19])=[CH:5][CH:6]=1

参加物

8

反応物 5

HCID 13441-PyrrolidineethanamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184502433-(3-Biphenyl-4-yl-ureido)-3-p-tolyl-propionic acidHCID 69431468HCID 69431468、化合物

生成物 1

HCID 10050407HCID 10050407、化合物収率 63%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

3-(3-Biphenyl-4-yl-ureido)-N-(2-pyrrolidin-1-yl-ethyl)-3-tolyl-propionamide. To a solution of 3-(3-biphenyl-4-yl-ureido)-3-p-tolyl-propionic acid (0.15 g, 0.40 mmol), 2-pyrrolidin-1-yl-ethylamine (0.05 g, 0.40 mmol) and HOBt (0.081 g, 0.60 mmol) in DMF (4 mL), was added EDCl (0.12 g, 0.60 mmol). The resulting solution was stirred under N2 at rt for 20 h. The solution was diluted with H2O (20 mL) and extracted with EtOAc (3×30 mL). The combined extracts were washed with brine (40 mL), dried (Na2SO4), and filtered, and the solvent was removed. The crude product was purified by column chromatography on silica gel using a gradient of 0–20% (MeOH(1% NH4OH)/CH2Cl2) to afford 0.12 g (63%) of the desired product as a white solid. Racemic compound: Rf=0.11 (10% MeOH (1% NH4OH)/CH2Cl2). MS (electrospray): mass calculated for C29H34N4O2, 470.27; m/z found, 471.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.57–7.50 (m, 4H), 7.43–7.37 (m, 4H), 7.29–7.25 (m, 3H), 7.16 (d, J=7.9 Hz, 2H), 5.22 (t, J=6.9 Hz, 1H), 3.28–3.23 (m, 2H), 2.68 (d, J=6.4 Hz, 2H), 2.52–2.48 (m, 6H), 2.31 (s, 3H), 1.77–1.75 (m, 4H).

後処理

  1. extractionextracted with EtOAc (3×30 mL)
  2. washThe combined extracts were washed with brine (40 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed
  6. customThe crude product was purified by column chromatography on silica gel using a gradient of 0–20% (MeOH(1% NH4OH)/CH2Cl2)

出典と根拠

ORDレコード
ord-f5281460bdb54dd7b86c787b843ba61b
出典データセット
uspto-grants-2007_04
特許番号
US07202269B2

反応ノート

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