Ammonium Acetate → HCID 10072381, 화합물

HRID 1245957노트

반응식

HRID 1245957 반응식
C([O-])(=O)C.[NH4+:5].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[C:29]3[C:28]([CH3:30])=[C:27]([CH3:31])[N:26]=[C:25](OC4C=CC=CC=4)[C:24]=3[N:23]=[C:22]2[CH2:39][CH2:40][CH3:41])(=[O:15])=[O:14])=[CH:9][CH:8]=1>>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]2[C:29]3[C:28]([CH3:30])=[C:27]([CH3:31])[N:26]=[C:25]([NH2:5])[C:24]=3[N:23]=[C:22]2[CH2:39][CH2:40][CH3:41])(=[O:15])=[O:14])=[CH:9][CH:8]=1

참가 물질

3

반응물 2

HCID 517165Ammonium AcetateHCID 21913047HCID 21913047, 화합물

생성물 1

HCID 10072381HCID 10072381, 화합물수율 28.2%

실험 절차

Ammonium acetate (20.2 g, 0.262 mol) and 1-[5-(4-chlorobenzenesulfonyl)pentyl]-6,7-dimethyl-4-phenoxy-2-propyl-1H-imidazo[4,5-c]pyridine (2.20 g, 4.18 mmol) were stirred at 160° C. in a sealed tube for 18 hours. The solution was allowed to cool to room temperature and partitioned between chloroform (50 mL) and water (25 mL). The aqueous solution was adjusted to pH 11 with the addition of 1 M sodium hydroxide and two solid sodium hydroxide pellets. The aqueous solution was then extracted with chloroform (4×50 mL). The combined organic solutions were washed with 1 M sodium hydroxide (2×25 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide the crude product as a tan foam. The crude product was purified by column chromatography on silica gel (eluting with 94:5:1 dichloromethane:methanol:triethylamine) to provide a product that was impure as determined by HPLC analysis. A second purification by column chromatography on silica gel (eluting with 96:3:1 dichloromethane:methanol:triethylamine) also resulted in impure material. The solid was recrystallized from acetonitrile, and the crystals were isolated by filtration, washed with cold acetonitrile and ethyl acetate, dried under high vacuum to provide 0.53 g of 1-[5-(4-chlorobenzenesulfonyl)pentyl]-6,7-dimethyl-2-propyl-1H-imidazo[4,5-c]pyridin-4-amine as white needles, mp 147.0–149.0° C.

후처리

  1. custompartitioned between chloroform (50 mL) and water (25 mL)
  2. additionThe aqueous solution was adjusted to pH 11 with the addition of 1 M sodium hydroxide and two solid sodium hydroxide pellets
  3. extractionThe aqueous solution was then extracted with chloroform (4×50 mL)
  4. washThe combined organic solutions were washed with 1 M sodium hydroxide (2×25 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto provide the crude product as a tan foam
  9. customThe crude product was purified by column chromatography on silica gel (eluting with 94:5:1 dichloromethane:methanol:triethylamine)
  10. customto provide a product that
  11. customA second purification by column chromatography on silica gel (eluting with 96:3:1 dichloromethane:methanol:triethylamine)
  12. customalso resulted in impure material
  13. customThe solid was recrystallized from acetonitrile
  14. customthe crystals were isolated by filtration
  15. washwashed with cold acetonitrile and ethyl acetate
  16. customdried under high vacuum

출처 및 근거

ORD 기록
ord-bccaea977966438382d1fea435af010c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125890B2

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