Ammonium Acetate → HCID 10072381, compound

HRID 1352609Notes

Reaction equation

HRID 1352609 reaction equation
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

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 21913047HCID 21913047, compound

Product 1

HCID 10072381HCID 10072381, compoundYield 28.2%

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-deecbbbc52c74b60a01331bd106006c4
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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