Methanol → HCID 124581090, compound

HRID 2121691Notes

Reaction equation

HRID 2121691 reaction equation
NC1N(C2C=CC(F)=CC=2)C(C2C=NC=CC=2)=CC=1C([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C@H:17]2[CH2:21][O:20]C(C)(C)[O:18]2)[CH:10]=1)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:48][OH:49]>O>[OH:18][C@@H:17]([CH2:21][OH:20])[CH2:16][O:15][C:11]1[CH:10]=[CH:9][CH:14]=[CH:13][C:12]=1[CH:48]=[O:49]

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 12114194HCID 12114194, compound

Product 1

HCID 124581090HCID 124581090, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.7 g (1.44 mmol) of [2-amino-1-(4-fluorophenyl)-5-pyridin-3-yl-1H-pyrrol-3-yl]-[3-(2,2-dimethyl-[1,3]dioxolan-4(S)-ylmethoxy)-phenyl]-methanone and 0.35 g of p-toluenesulfonic acid in 20 mL of methyl alcohol and 5 mL of water was heated to 50°. After 18 h, the reaction mixture was cooled to room temperature and the solvent was concentrated under reduced pressure. The residue was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The product was purified by flash chromatography (gradient elution: 100% ethyl acetate-10% methyl alcohol/ethyl acetate/0.4% ammonium hydroxide). The purified product was converted to a HCl salt by treatment of an ethyl acetate solution with HCl/ether. The salt was isolated by filtration and dried to give 0.4 g (56%) of 2-amino-1-(4-fluorophenyl)-5-pyridin-3-yl-1H-pyrrol-3-yl]-3-{[2(S), 3dihydroxypropoxy]phenyl}-methanone (MH+=448).

Workup

  1. temperaturewas heated to 50°
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe residue was partitioned between aqueous sodium bicarbonate and ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe product was purified by flash chromatography (gradient elution: 100% ethyl acetate-10% methyl alcohol/ethyl acetate/0.4% ammonium hydroxide)
  8. customThe salt was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-9ebbcf4c088f4acc84771ac8d9a42ebb
Source dataset
uspto-grants-2004_02
Patent number
US06696471B2

Reaction notes

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