1,1'-Carbonyldiimidazole → 3-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-urea

HRID 2223713

반응식

HRID 2223713 반응식
[CH:1]1N=[CH:4][N:3]([C:6]([N:8]2[CH:12]=[N:11][CH:10]=[CH:9]2)=[O:7])[CH:2]=1.[CH2:13]([CH:20]1[CH2:25][CH2:24]N(CCN)C[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CNC1C2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=[C:33]([CH3:41])[CH:32]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CS(C)=O.O>[CH2:13]([CH:20]1[CH2:21][CH2:12][N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[N:3]([CH3:4])[C:2]2[C:1]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[N:34]=[C:33]([CH3:41])[CH:32]=2)[CH2:24][CH2:25]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

7

반응물 4

HCID 682631,1'-CarbonyldiimidazoleHCID 2724254Sodium bis(trimethylsilyl)amideHCID 27798312-(4-Benzylpiperidin-1-yl)ethan-1-amineHCID 13042979N,2-dimethylquinolin-4-amine

생성물 1

HCID 179564923-[2-(4-Benzyl-piperidin-1-yl)-ethyl]-1-methyl-1-(2-methyl-quinolin-4-yl)-urea

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

반응 조건

온도
20 °C

실험 절차

To a stirred solution of CDI (178 mg, 1.1 mmol) in DMSO (5 mL) is added a solution of 2-(4-benzyl-piperidin-1-yl)-ethylamine (218 mg, 1 mmol) in DMSO (1 mL). The reaction mixture is stirred at 20° C. for 3 h. Methyl-(2-methyl-quinolin-4-yl)-amine (173 mg, 1 mmol) is added. To the resulting solution is added in a single portion NaHMDS (2 M in THF, 1.25 mL, 2.5 mmol). The reaction mixture is stirred at 20° C. for 24 h, then H2O (0.4 mL) is added. The reaction mixture is evaporated and the residue purified by preparative HPLC to provide the title compound.

후처리

  1. stirringThe reaction mixture is stirred at 20° C. for 24 h
  2. customThe reaction mixture is evaporated
  3. customthe residue purified by preparative HPLC

출처 및 근거

ORD 기록
ord-3925a18c660d4ba7bf8c3fa196ebf96e
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07375227B2

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