Sodium Chloride → HCID 25151202, compound

HRID 2370306Notes

Reaction equation

HRID 2370306 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][N:17]=[CH:18]2)=[CH:13][C:12]=1F.[Cl-].[Na+].C[N:25]([CH:27]=O)C>C(OCC)(=O)C>[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][N:17]=[CH:18]2)=[CH:13][C:12]=1[O:7][CH:1]1[CH2:6][CH2:5][C:4]([CH2:27][NH2:25])([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 534189227-Chloro-6-fluoroisoquinoline

Product 1

HCID 25151202HCID 25151202, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

123.3 mg of 4-aminomethyl-4-phenyl)-cyclohexanol were dissolved in 4 mL of dry DMF and 60 mg of sodium hydride were added. The mixture was allowed to stir for 20 minutes, then 91 mg of 7-Chloro-6-fluoro-isoquinoline (4) were added. Stirring at room temperature was continued until conversion was complete. Ethyl acetate and saturated sodium chloride solution were added. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, concentrated and the resultant residue was purified via preparative HPLC. The obtained TFA salt was dissolved in 2 N HCl and evaporated. After dissolving the residue in water and lyophilization, the title compound was isolated as the hydrochloride. Rt=0.97 min (Method B). Detected mass: 367.2 (M+H+).

Workup

  1. stirringStirring at room temperature
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe resultant residue was purified via preparative HPLC
  7. dissolutionThe obtained TFA salt was dissolved in 2 N HCl
  8. customevaporated
  9. dissolutionAfter dissolving the residue in water

Sources & evidence

ORD record
ord-a9832df54f85447c8045faf0b808e1a3
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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