1-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chloride → 1-Allyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amide

HRID 1259390Notes

Reaction equation

HRID 1259390 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.[CH2:22]([C:25]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26]1)[CH:23]=[CH2:24]>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]([C:25]2([CH2:22][CH:23]=[CH2:24])[CH2:27][CH2:26]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 441819591-(Prop-2-en-1-yl)cyclopropane-1-sulfonyl chlorideHCID 58380528HCID 58380528, compound

Product 1

HCID 583805551-Allyl-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 34.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Using the same reaction conditions and workup 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: 0.46 g, 0.001 mol) in dry pyridine (3 mL) was reacted with 1-allyl-cyclopropane sulfonyl chloride (0.25 g, 0.0014 mol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in DCM) afforded 0.19 g of the product (30% 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 DCM)

Sources & evidence

ORD record
ord-a59fad67ebff4bd09242300d4f37bd1e
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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