Hydrochloric Acid → HCID 59443072, compound

HRID 1959128Notes

Reaction equation

HRID 1959128 reaction equation
Cl.[C:2]([C:4]1[C:5]([CH3:30])([CH3:29])[O:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[CH:11][CH:10]=[C:9]([NH:21]C(=O)OC(C)(C)C)[CH:8]=2)#[N:3].[O:31]1CCOCC1>>[NH2:21][C:9]1[CH:8]=[C:7]2[C:12]([C:13]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[C:4]([C:2]([NH2:3])=[O:31])[C:5]([CH3:30])([CH3:29])[O:6]2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59443032HCID 59443032, compound

Product 1

HCID 59443072HCID 59443072, compound

Procedure

6N Hydrochloric acid (15 mL) was added to a solution of tert-butyl [3-cyano-4-(4-fluorophenyl)-2,2-dimethyl-2H-chromen-7-yl]carbamate (a compound obtained in Reference Example 8(3); 150 mg) in dioxane (5 mL) and the mixture was heated under reflux for 90 hours. The reaction solution was concentrated in vacuo, the resulted residue was diluted with ethyl acetate and washed with a saturated solution of sodium bicarbonate and brine. The organic layer was filtered through a column of porous diatomite (Chem Elut) and the filtrate was concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent: chloroform/methanol=100/0 to 95/5) to give the titled compound (26 mg) as a yellow powder.

Workup

  1. customobtained in Reference Example 8(3)
  2. temperatureunder reflux for 90 hours
  3. concentrationThe reaction solution was concentrated in vacuo
  4. additionthe resulted residue was diluted with ethyl acetate
  5. washwashed with a saturated solution of sodium bicarbonate and brine
  6. filtrationThe organic layer was filtered through a column of porous diatomite (Chem Elut)
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe resultant residue was purified by column chromatography on silica gel (Solvent: chloroform/methanol=100/0 to 95/5)

Sources & evidence

ORD record
ord-1510219ec46e4a468ceeabcfaa187555
Source dataset
uspto-grants-2013_04
Patent number
US08410166B2

Reaction notes

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