Ethyl 2-chloroethanecarboximidate hydrochloride → tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate

HRID 1364077노트

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HRID 1364077 반응식
[NH2:1][C:2]1[C:3]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:4][C:5]([CH3:21])=[C:6]([CH3:20])[C:7]=1[NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].Cl.[Cl:30][CH2:31][C:32](=N)OCC>C(Cl)(Cl)Cl>[Cl:30][CH2:31][C:32]1[N:8]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]2[C:6]([CH3:20])=[C:5]([CH3:21])[N:4]=[C:3]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:2]=2[N:1]=1

참가 물질

4

반응물 2

HCID 12470659Ethyl 2-chloroethanecarboximidate hydrochlorideHCID 21973822Tert-butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate

생성물 1

HCID 66957882tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate수율 115.7%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

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온도
60 °C

실험 절차

tert-Butyl 3-[(3-amino-5,6-dimethyl-2-phenoxypyridin-4-yl)amino]propylcarbamate (68.8 g, 178 mmol), prepared as described in U.S. Pat. No. 6,545,016, Example 17, Parts A through C, was dissolved in chloroform (600 mL). Ethyl 2-chloroacetimidate hydrochloride (56.0 g, 354 mmol) was added to the solution and the reaction mixture was stirred at 60° C. for 72 hours. The reaction mixture was diluted with chloroform (200 mL), washed with brine (2×600 mL), and the layers were separated. The combined organics were dried over magnesium sulfate, filtered through CELITE filter aid, and concentrated under reduced pressure to afford 91.62 g of tert-butyl 3-[2-(chloromethyl)-6,7-dimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl]propylcarbamate.

후처리

  1. washwashed with brine (2×600 mL)
  2. customthe layers were separated
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. filtrationfiltered through CELITE
  5. filtrationfilter aid
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-ba661bdab33b4c02933d9f590fea6437
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888349B2

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