Water → HCID 11340110, compound

HRID 2217892Notes

Reaction equation

HRID 2217892 reaction equation
[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][C:20]#N)[CH2:13]1)[CH:6]=[CH:5]2.[OH-:32].[K+].[OH2:34]>CO>[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:31])[CH2:24][CH:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][CH2:18][CH2:19][C:20]([OH:34])=[O:32])[CH2:13]1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 68809044HCID 68809044, compound

Product 1

HCID 11340110HCID 11340110, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-[6-Chloro-2-[(3S)-3-[(2-cyanoethyl)amino]-1-pyrrolidinyl]-5-quinolinyl]-cyclohexaneacetamide (0.1 g), potassium hydroxide (0.051 g), water (1 mL) and methanol (2 mL) were heated within a single mode microwave in a sealed 10 mL vial for 100 minutes at 90° C. The resulting mixture was dissolved in methanol (20 mL) and purified on a Varian® SCX cartridge, washed with methanol (50 mL) and eluted with ammonia in methanol (0.7M, 50 mL). The residue was further purified on a Varian® NH2 cartridge washed with methanol (50 mL) and eluted with acetic acid:methanol (10:90). The solvent was removed under vacuum and the residue triturated with hot methanol, cooled and filtered to afford the title compound (7 mg).

Workup

  1. custompurified on a Varian® SCX cartridge
  2. washwashed with methanol (50 mL)
  3. washeluted with ammonia in methanol (0.7M, 50 mL)
  4. customThe residue was further purified on a Varian® NH2 cartridge
  5. washwashed with methanol (50 mL)
  6. washeluted with acetic acid:methanol (10:90)
  7. customThe solvent was removed under vacuum
  8. customthe residue triturated with hot methanol
  9. temperaturecooled
  10. filtrationfiltered

Sources & evidence

ORD record
ord-ef5cc5b4f83445f793d5759552e9393b
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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