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Ethyl Acetate → 8-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

HRID 1259375
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1259375
[C:1]([O:5][C:6]([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]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].C(OC(=O)C)C>O.C1COCC1.[Zn]>[C:1]([O:5][C:6]([N:8]1[C:12]2=[C:13]([NH2:28])[C:14]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=3[F:27])=[C:15]([CH3:18])[C:16](=[O:17])[N:11]2[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]
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Komponenten

7

Edukt 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 671987717-(2-fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 671938118-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl esterAusbeute 87,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Zinc (296 mg, 0.005 mol) was added to a stirred solution of 7-(2-fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-5-oxo-2,3-dihydro-5H-imidazo[1,2-a]pyridine-1-carboxylic acid tert-butyl ester (400 mg, 0.0008 mol) and NH4Cl (322 mg, 0.006 mol) in water and THF (15 mL). The resulting mixture was stirred at room temperature for 30 minutes. The reaction 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 350 mg of the crude product which was used in the next step without further purification.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-971b2560ad784c74bb7dba789b394ab7
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08466289B2

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