Hydrochloric Acid → HCID 11486057, compound

HRID 2217868Notes

Reaction equation

HRID 2217868 reaction equation
[OH-:1].[K+].[Cl:3][C:4]1[C:5]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:14][CH2:15][CH2:16][C:17]#N)[CH:8]=[CH:7]2.Cl.C[OH:31]>>[Cl:3][C:4]1[C:5]([NH:19][C:20](=[O:28])[CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([CH2:14][CH2:15][CH2:16][C:17]([OH:31])=[O:1])[CH:8]=[CH:7]2

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14797Potassium HydroxideHCID 68809609N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide

Product 1

HCID 11486057HCID 11486057, compound

Conditions

Temperature
50 °C

Procedure

Potassium hydroxide (2 mL, 50% solution in water) was added to a stirred solution of N-[6-chloro-2-(3-cyanopropyl)-5-quinolinyl]-cyclohexaneacetamide (Example 67(a)) (190 mg) in methanol (2 mL). The reaction mixture was heated to 50° C. for 6 hours then allowed to cool. The mixture was acidified with aqueous 2M hydrochloric acid until a precipitate formed which was collected by filtration. Purification by HPLC (Symmetry—0.1% aqueous ammonium acetate/acetonitrile) afforded the title compound as a solid (45 mg).

Workup

  1. temperatureto cool
  2. customformed which
  3. filtrationwas collected by filtration
  4. customPurification by HPLC (Symmetry—0.1% aqueous ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-6f7aee50ec254050841721b101d37feb
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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