Hydrochloric Acid → HCID 20770841, compound

HRID 1296050Notes

Reaction equation

HRID 1296050 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][C:16](=[O:33])[CH2:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([S:27][CH2:28][CH2:29][CH:30]=O)=[CH:21][C:20]=1[CH3:32].CC1C=CC(S(O)(=O)=O)=CC=1.Cl.C(=O)(O)[O-].[Na+]>CO>[CH3:14][O:15][C:16](=[O:33])[CH2:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[C:22]([S:27][CH2:28][CH2:29][CH2:30][NH:13][C:10]2[CH:9]=[CH:8][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:12][N:11]=2)=[CH:21][C:20]=1[CH3:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 1050975-Phenyl-2-pyridinamineHCID 516892Sodium BicarbonateHCID 20770844HCID 20770844, compound

Product 1

HCID 20770841HCID 20770841, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Commercially available 5-phenyl-pyridin-2-ylamine (631 mg, 3.7 mmol) and Compound 64A were dissolved in 20 ml methanol with catalytic p-TsOH (ca. 20 mg) and stirred at 25 C for 18 h to give a yellow solution. NaH3CN was added and the reaction was allowed to stir for 1 h. 2N HCl was added to pH<3 and stirred 5 minutes. Saturated sodium bicarbonate was added and the product was extracted in to 100 ml ethyl acetate, dried over anhydrous sodium sulfate, decanted and concentrated. Liquid chromatography gave the title compound as a white solid. MS m/z 453 (M+1).

Workup

  1. customto give a yellow solution
  2. stirringto stir for 1 h
  3. stirringstirred 5 minutes
  4. extractionthe product was extracted in to 100 ml ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. customdecanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-3ebf079fce424df78bcb8a1f80d1594f
Source dataset
uspto-grants-2007_07
Patent number
US07244763B2

Reaction notes

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