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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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N-Methyl-N-nitrosourea → 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(cyclopropylmethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

HRID 1874926
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HRID 1874926 반응식
[OH-].[K+].[CH3:3]N(N=O)C(N)=O.[Cl:10][C:11]1[N:12]=[CH:13][N:14]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:15]=1[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][C:28]2[CH:33]=[C:32]([CH2:34][CH:35]=[CH2:36])[CH:31]=[C:30]([C:37]#[N:38])[CH:29]=2)[C:21]=1[F:39])=[O:17]>C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:10][C:11]1[N:12]=[CH:13][N:14]([CH2:40][O:41][CH2:42][CH2:43][Si:44]([CH3:47])([CH3:46])[CH3:45])[C:15]=1[C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([O:27][C:28]2[CH:33]=[C:32]([CH2:34][CH:35]3[CH2:3][CH2:36]3)[CH:31]=[C:30]([C:37]#[N:38])[CH:29]=2)[C:21]=1[F:39])=[O:17]
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참가 물질

6

반응물 3

HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 684834184-chloro-N-[(4-chloro-3-{[3-cyano-5-(2-propen-1-yl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

생성물 1

HCID 684866314-chloro-N-[(4-chloro-3-{[3-cyano-5-(cyclopropylmethyl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 3283Diethyl Ether용매2회

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온도
0 °C

실험 절차

To a mixture of 30% aqueous KOH (11 mL) and diethyl ether (11 mL) was added N-methyl-N-nitrosourea (0.097 g, 0.938 mmol) in one portion with stirring and cooling at 0° C. and the reaction mixture was maintained at this temperature for 20 min. The organic phase was isolated, dried over KOH pellets and added dropwise to a solution of 4-chloro-N-[(4-chloro-3-{[3-cyano-5-(2-propen-1-yl)phenyl]oxy}-2-fluorophenyl)methyl]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.054 g, 0.094 mmol) and palladium(II) acetate (2.106 mg, 9.38 μmol) in diethyl ether (11.00 mL) with stirring and cooling at 0° C. The reaction mixture was stirred at 0° C. for 1 h and then allowed to warm to room temperature and stirred overnight at which time LC-MS indicated complete conversion to desired product.

후처리

  1. temperaturethe reaction mixture was maintained at this temperature for 20 min
  2. customThe organic phase was isolated
  3. dry with materialdried over KOH pellets
  4. stirringwith stirring
  5. temperaturecooling at 0° C
  6. stirringThe reaction mixture was stirred at 0° C. for 1 h
  7. temperatureto warm to room temperature
  8. stirringstirred overnight at which time LC-MS

출처 및 근거

ORD 기록
ord-0f6aa9817c744024ad68568792403f00
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304419B2

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