3-(Benzyloxy)cyclobutane-1-sulfonyl chloride → 3-Benzyloxy-cyclobutanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259431Notes

Reaction equation

HRID 1259431 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.[CH2:22]([O:29][CH:30]1[CH2:33][CH:32]([S:34](Cl)(=[O:36])=[O:35])[CH2:31]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>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:34]([CH:32]2[CH2:33][CH:30]([O:29][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:31]2)(=[O:36])=[O:35])=[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 583805353-(Benzyloxy)cyclobutane-1-sulfonyl chlorideHCID 583805858-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-thiazolo[3,2-a]pyridin-5-one

Product 1

HCID 583805773-Benzyloxy-cyclobutanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyridin-8-yl]-amideYield 44.5%

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: 0.15 g, 0.35 mmol) in pyridine (2 mL) was reacted with 3-benzyloxy-cyclobutanesulfonyl chloride (0.1 g, 0.39 mmol) to afford the crude product. Purification by column chromatography on silica gel (50% ethylacetate in hexane) afforded 0.1 g of the product (43% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (50% ethylacetate in hexane)

Sources & evidence

ORD record
ord-71daf5b8b8174b44accbad4e422ac0d6
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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