Hydrochloric Acid → 8-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

HRID 1259420Notes

Reaction equation

HRID 1259420 reaction equation
Cl.Cl[Sn]Cl.O.[F:6][C:7]1[CH:12]=[C:11]([I:13])[CH:10]=[CH:9][C:8]=1[NH:14][C:15]1[C:16]([N+:26]([O-])=O)=[C:17]2[S:25][CH2:24][CH2:23][N:18]2[C:19](=[O:22])[C:20]=1[CH3:21].C(=O)(O)[O-]>C(O)C.C(Cl)Cl.C(OC(=O)C)C>[NH2:26][C:16]1[C:15]([NH:14][C:8]2[CH:9]=[CH:10][C:11]([I:13])=[CH:12][C:7]=2[F:6])=[C:20]([CH3:21])[C:19](=[O:22])[N:18]2[CH2:23][CH2:24][S:25][C:17]=12

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 769Bicarbonate IonHCID 43835034Tin dichloride dihydrateHCID 583805407-(2-Fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Product 1

HCID 583805858-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-oneYield 98%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Concentrated HCl (0.3 mL) and SnCl2.H2O (0.15 g, 0.671 mmol) were added to 7-(2-fluoro-4-iodo-phenylamino)-6-methyl-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one (0.1 g, 0.22 mmol) in ethanol (3 mL). The resulting mixture was heated to reflux for 2 hours. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was cooled to room temperature, diluted with DCM, basified with saturated bicarbonate solution and filtered through celite. The filtrate was extracted with DCM. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 0.09 g of the product (90% yield).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through celite
  4. extractionThe filtrate was extracted with DCM
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29621328131b4a9c902b988bcb36b70c
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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