Dimethylsulphamoyl chloride → N-[7-(2-Fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-dimethylaminosulfonamide

HRID 1259426Notes

Reaction equation

HRID 1259426 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][C:10]=2[F:16])=[C:6]([CH3:17])[C:5](=[O:18])[N:4]2[CH2:19][CH2:20][S:21][C:3]=12.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>N1C=CC=CC=1>[F:16][C:10]1[CH:11]=[C:12]([I:15])[CH:13]=[CH:14][C:9]=1[NH:8][C:7]1[C:2]([NH:1][S:24]([N:23]([CH3:28])[CH3:22])(=[O:26])=[O:25])=[C:3]2[S:21][CH2:20][CH2:19][N:4]2[C:5](=[O:18])[C:6]=1[CH3:17]

Participants

4

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 583805858-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Product 1

HCID 52934558N-[7-(2-Fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-dimethylaminosulfonamideYield 317.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and workup as described for the preparation of Example 19A, 8-amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one (I-19f: 0.2 g, 0.048 mmol) in pyridine (2 mL) was reacted with dimethyl aminosulfonyl chloride (76 mg, 0.528 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 0.08 g of the product (32% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (2% MeOH in CHCl3)

Sources & evidence

ORD record
ord-6de079ca80134101a73d9cd6b254c445
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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