Hydrochloric Acid → HCID 13746697, compound

HRID 1731626Notes

Reaction equation

HRID 1731626 reaction equation
[CH2:1]1[C:21]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]([NH2:19])=O)[CH:15]=[CH:16][C:10]=4[CH:9]=[CH:8][C:7]=3[CH:20]=2)[CH2:3][CH2:2]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.Cl>N1C=CC=CC=1>[CH2:1]1[C:21]2[C:4](=[CH:5][C:6]3[S:12][C:11]4[CH:13]=[C:14]([C:17]#[N:19])[CH:15]=[CH:16][C:10]=4[CH:9]=[CH:8][C:7]=3[CH:20]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9845Trifluoroacetic anhydrideHCID 13746696HCID 13746696, compound

Product 1

HCID 13746697HCID 13746697, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The crude amide from Step A (4.34 g, 14.8 mmole) in pyridine (43.5 ml) was treated slowly under cooling (ice-bath) with trifluoroacetic anhydride (8.7 ml). The mixture was stirred for 1 hour at ambient temperature and then poured into a mixture of ice (400 g) and concentrated hydrochloric acid (50 ml). The product was extracted into ether and the ethereal extract was washed with water, then with 10% sodium carbonate solution and finally with saturated sodium chloride solution. After drying (MgSO4) the solution was evaporated to a tan colored solid (3.22 g). The product was purified by chromatography on Merck silica gel using toluene as solvent to give 2.45 g of the title compound. Melting point 142°-143° C. (from acetonitrile).

Workup

  1. extractionThe product was extracted into ether
  2. extractionthe ethereal extract
  3. washwas washed with water
  4. dry with materialAfter drying (MgSO4) the solution
  5. customwas evaporated to a tan colored solid (3.22 g)
  6. customThe product was purified by chromatography on Merck silica gel

Sources & evidence

ORD record
ord-faf6778b1aa84b4b9279424c35753126
Source dataset
uspto-grants-1986_11
Patent number
US04622403

Reaction notes

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