Triethylamine → N-(4-chloro-2-methylphenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)urea

HRID 1162360

반응식

HRID 1162360 반응식
Cl.Cl.[NH2:3][CH:4]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:5]([N:7]1[CH2:12][CH2:11][CH:10]([N:13]2[CH2:17][C:16]3=[CH:18][N:19]=[C:20]([CH3:21])[N:15]3[C:14]2=[O:22])[CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C.[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]=[C:44]=[O:45])=[C:39]([CH3:46])[CH:38]=1>C(#N)C>[Cl:36][C:37]1[CH:42]=[CH:41][C:40]([NH:43][C:44]([NH:3][CH:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:5]([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[CH2:17][C:16]4=[CH:18][N:19]=[C:20]([CH3:21])[N:15]4[C:14]3=[O:22])[CH2:9][CH2:8]2)=[O:6])=[O:45])=[C:39]([CH3:46])[CH:38]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1421574-Chloro-2-methylphenyl isocyanateHCID 23138338HCID 23138338, 화합물

생성물 1

HCID 23138117N-(4-chloro-2-methylphenyl)-N'-(2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethyl)urea수율 64.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-(1-(2-Amino-2-phenylacetyl)-4-piperidinyl)-5-methyl-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one dihydrochloride (0.21 g) obtained in Example 115a) was dissolved in acetonitrile (5.0 ml). Triethylamine (0.14 ml) and 4-chloro-2-methylphenyl isocyanate (80 mg) were added thereto, and mixed at room temperature for 15 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate. The reaction mixture was washed with an aqueous sodium hydrogen carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified with basic silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate). The product was crystallized from ethyl acetate-diethyl ether to obtain the title compound as colorless powder (0.16 g, 61%).

후처리

  1. additionmixed at room temperature for 15 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe reaction mixture was washed with an aqueous sodium hydrogen carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified with basic silica gel column (ethyl acetate/hexane=1/1 to ethyl acetate)
  8. customThe product was crystallized from ethyl acetate-diethyl ether

출처 및 근거

ORD 기록
ord-2892fbdaf70440ae97e28f2102919493
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07820673B2

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