Hydrochloric Acid → 5-(5-Cyanopentyl)-imidazo[1,5-a]pyridine

HRID 2417833Notes

Reaction equation

HRID 2417833 reaction equation
S(Cl)(Cl)=O.[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]2[CH:19]=[N:20][CH:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1)(O)=O.S(N)([NH2:25])(=O)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>S1(CCCC1)(=O)=O>[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:18]2[CH:19]=[N:20][CH:21]=[C:17]2[CH:16]=[CH:15][CH:14]=1)#[N:25]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 55390PirmagrelHCID 82267SulfamideHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 155864755-(5-Cyanopentyl)-imidazo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

Thionyl chloride (11.42 g) is added slowly at room temperature to a suspension of 5-(5-carboxypentyl)imidazo[1,5-a]pyridine (21.0 g) and sulfamide (10.5 g) in 90 ml of sulfolane. The mixture is heated at 120° until gas evolution ceases and solid p-toluenesulfonic acid monohydrate (1.71 g) is added carefully. After heating an additional 3 hours at 120°, the reaction mixture is cooled, poured onto 200 g of ice and acidified with 130 ml of 1N hydrochloric acid. The aqueous phase is sequentially extracted with ethyl acetate (3×100 ml), made basic with solid sodium bicarbonate and reextracted with ethyl acetate (3×125 ml). The organic extracts are washed with 0.5N sodium hydroxide (5×50 ml), dried over sodium sulfate and evaporated to yield an oil which is chromatographed on 60 g of silica gel with ethyl acetate to yield 5-(5-cyanopentyl)-imidazo[1,5-a]pyridine as an oil.

Workup

  1. additionis added carefully
  2. temperatureAfter heating an additional 3 hours at 120°
  3. temperaturethe reaction mixture is cooled
  4. extractionThe aqueous phase is sequentially extracted with ethyl acetate (3×100 ml)
  5. washThe organic extracts are washed with 0.5N sodium hydroxide (5×50 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto yield an oil which
  9. customis chromatographed on 60 g of silica gel with ethyl acetate

Sources & evidence

ORD record
ord-24d46e515dbb4c509543c4128f6afa13
Source dataset
uspto-grants-1984_09
Patent number
US04470986

Reaction notes

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