Pyridine → HCID 69192953, compound

HRID 132845Notes

Reaction equation

HRID 132845 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[C:13](Cl)[C:12]([C:19](OCC)=O)=[CH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].CS(Cl)(=O)=O.[N:32]1C=CC=CC=1>O1CCCC1.CO.O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[N:14]=[CH:13][C:12]([C:19]#[N:32])=[CH:11][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chloride2×HCID 168937Lithium hydroxide, monohydrateHCID 86604213HCID 86604213, compound

Product 1

HCID 69192953HCID 69192953, compound

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of the product from Step A above in 6 mL of 3:2:1 tetrahydrofuran/methanol/water was added lithium hydroxide monohydrate (0.23 g, 5.58 mmol). The mixture was allowed to stir overnight and the volatiles were removed under reduced pressure. Additional water was added, and the solution was acidified with citric acid monohydrate. The resultant precipitate was collected, washed with water, and dried in vacuo. To an ice-cold solution of this intermediate (1.0 g, 3.6 mmol) in 32 mL of pyridine was added methanesulfonyl chloride (0.41 g, 3.6 mmol) dropwise, and the resultant mixture was allowed to stir for one hour. Dry ammonia gas was bubbled into the reaction mixture for 2 minutes. The excess ammonia was then removed under reduced pressure, and the solution was cooled again in ice and treated with methanesulfonyl chloride (3.43 g, 30.0 mmol). The resultant mixture was allowed to warm to room temperature overnight. The reaction was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The product was extracted with ethyl acetate, and the combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The resultant crystalline solid was triturated with ether, and the precipitate was collected to afford the title compound as a light orange powder.

Workup

  1. customthe volatiles were removed under reduced pressure
  2. additionAdditional water was added
  3. customThe resultant precipitate was collected
  4. washwashed with water
  5. customdried in vacuo
  6. stirringto stir for one hour
  7. customDry ammonia gas was bubbled into the reaction mixture for 2 minutes
  8. customThe excess ammonia was then removed under reduced pressure
  9. temperaturethe solution was cooled again in ice
  10. concentrationThe reaction was concentrated under reduced pressure
  11. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  12. extractionThe product was extracted with ethyl acetate
  13. dry with materialthe combined extracts were dried over magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe resultant crystalline solid was triturated with ether
  16. customthe precipitate was collected

Sources & evidence

ORD record
ord-6080a914a7b74000b0c4340792a5b857
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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