1-Pyrrolidineethanamine → HCID 10050407, 화합물

HRID 1270984노트

반응식

HRID 1270984 반응식
[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

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 10050407HCID 10050407, 화합물수율 63%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f5281460bdb54dd7b86c787b843ba61b
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202269B2

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