(3-Methyloxetan-3-yl)methanesulfonyl chloride → N-(7-(2-fluoro-4-iodophenylamino)-6-methyl-5-oxo-3,5-dihydro-2H-oxazolo[3,2-a]pyridin-8-yl)-1-(3-methyloxetan-3-yl)methanesulfonamide

HRID 1259411Notes

Reaction equation

HRID 1259411 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][O:21][C:3]=12.[CH3:22][C:23]1([CH2:27][S:28](Cl)(=[O:30])=[O:29])[CH2:26][O:25][CH2:24]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:28]([CH2:27][C:23]2([CH3:22])[CH2:26][O:25][CH2:24]2)(=[O:30])=[O:29])=[C:3]2[O:21][CH2:20][CH2:19][N:4]2[C:5](=[O:18])[C:6]=1[CH3:17]

Participants

4

Reactant 2

HCID 53484656(3-Methyloxetan-3-yl)methanesulfonyl chlorideHCID 58380528HCID 58380528, compound

Product 1

HCID 52934327N-(7-(2-fluoro-4-iodophenylamino)-6-methyl-5-oxo-3,5-dihydro-2H-oxazolo[3,2-a]pyridin-8-yl)-1-(3-methyloxetan-3-yl)methanesulfonamideYield 9.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and procedure as described for the preparation of Example 7A, 8-Amino-7-(2-fluoro-4-iodo-phenylamino)-6-methyl-2,3-dihydro-oxazolo[3,2-a]pyridin-5-one (I-7f: 0.2 g, 0.499 mmol) was reacted with (3-methyloxetan-3-yl)methanesulfonyl chloride (0.13 g, 0.748 mmol) in dry pyridine (3 mL) to afford the crude product. Purification by preparative HPLC afforded 25 mg of the product (9% yield).

Workup

  1. customthe same reaction conditions and procedure
  2. customto afford the crude product
  3. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-b7123fbb4a4745d9a715282586700b1e
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…