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

HRID 1259436Notes

Reaction equation

HRID 1259436 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[C:11]([N+:20]([O-])=O)=[C:12]2[S:19][CH2:18][CH2:17][N:13]2[C:14](=[O:16])[CH:15]=1.Cl[Sn]Cl.O.Cl>C(O)C>[NH2:20][C:11]1[C:10]([NH:9][C:3]2[CH:4]=[CH:5][C:6]([I:8])=[CH:7][C:2]=2[F:1])=[CH:15][C:14](=[O:16])[N:13]2[CH2:17][CH2:18][S:19][C:12]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 43835034Tin dichloride dihydrateHCID 583805547-(2-Fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Product 1

HCID 583805768-Amino-7-(2-fluoro-4-iodo-phenylamino)-2,3-dihydro-thiazolo[3,2-a]pyridin-5-oneYield 109.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Using the same reaction conditions and workup as described for the preparation of Intermediate (I-19f), 7-(2-fluoro-4-iodo-phenylamino)-8-nitro-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one (0.08 g, 0.181 mmol) in ethanol (2 mL) was reacted with SnCl2.H2O (0.12 g, 0.541 mmol) and concentrated HCl (0.5 mL) to afford 0.08 g of crude product which was used in the next step without further purification. LCMS: 59%, m/z=403.9 (M+1).

Workup

  1. customthe same reaction conditions and workup

Sources & evidence

ORD record
ord-2c098f7eed9348eca52d69ff6a325900
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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