Hydrochloric Acid → HCID 178522851, compound

HRID 1181457Notes

Reaction equation

HRID 1181457 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.Cl.C1C[O:31]CC1>C(OCC)(=O)C>[OH:31][C:2]1[C:11]2[C:6](=[C:7]([NH:12][C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[O:14])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8028TetrahydrofuranHCID 99997771-(1-Chloro-isoquinolin-5-yl)-3-(4-trifluoromethyl-benzyl)-urea

Product 1

HCID 178522851HCID 178522851, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

N-(1-chloroisoquinolin-5-yl)-N′-[4-(trifluoromethyl)benzyl]urea (Example 69; 47 mg, 0.12 mmol) was added to a mixture of 3N HCl (aq. 5 ml) and THF (1 ml). The mixture was heated at 90° C. for 20 hours, then 5N HCl (aq. 2 ml) was added and the reaction heated at 90° C. for a further 20 hours. After cooling to room temperature, ethyl acetate (20 ml) was added and the layers separated (some solid was suspended in the organic layer). The organic phase was washed with saturated aqueous NaHCO3 (20 ml), then evaporated. The residue was triturated in refluxing isopropyl alcohol (5 ml), then cooled to room temperature. The white solid was collected by filtration and washed with isopropyl alcohol (2×1 ml) to give the title compound (22 mg). m/z (ES+) 362 (M+H)+.

Workup

  1. temperaturethe reaction heated at 90° C. for a further 20 hours
  2. temperatureAfter cooling to room temperature
  3. customthe layers separated (some solid
  4. washThe organic phase was washed with saturated aqueous NaHCO3 (20 ml)
  5. customevaporated
  6. customThe residue was triturated
  7. temperaturein refluxing isopropyl alcohol (5 ml)
  8. temperaturecooled to room temperature
  9. filtrationThe white solid was collected by filtration
  10. washwashed with isopropyl alcohol (2×1 ml)

Sources & evidence

ORD record
ord-aa62680cff6f44ccad3ebd637cee45b0
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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