Ethyl Acetate → HCID 67192849, compound

HRID 1259362Notes

Reaction equation

HRID 1259362 reaction equation
[CH2:1]([N:8]1[C:12]2=[C:13]([N+:28]([O-])=O)[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)C>C1COCC1.Cl.[Zn]>[NH2:28][C:13]1[C:14]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Br:26])=[CH:22][C:21]=2[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12]=12

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 67194489HCID 67194489, compound

Product 1

HCID 67192849HCID 67192849, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Zinc (414 mg, 0.006 mol) was added to a stirred solution of 1-benzyl-7-(4-bromo-2-fluoro-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one (500 mg, 0.001 mol) in THF (50 mL) and concentrated HCl (1 mL). The resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was monitored by TLC (100% ethylacetate). The reaction mixture was concentrated and partitioned between ethylacetate and water. The organic layer was washed with saturated NaHCO3 solution and concentrated to afford 400 mg of the crude product which was used in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethylacetate and water
  3. washThe organic layer was washed with saturated NaHCO3 solution
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5c4766f447864a77af6e5407bee38fa6
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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