HCID 58380528, compound → 1-(3-Benzyloxy-propyl)-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 1259396Notes

Reaction equation

HRID 1259396 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]([O:29][CH2:30][CH2:31][CH2:32][C:33]1([S:36](Cl)(=[O:38])=[O:37])[CH2:35][CH2:34]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:36]([C:33]2([CH2:32][CH2:31][CH2:30][O:29][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:35][CH2:34]2)(=[O:38])=[O:37])=[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 58380528HCID 58380528, compoundHCID 866563321-[3-(Benzyloxy)propyl]cyclopropane-1-sulfonyl chloride

Product 1

HCID 583805701-(3-Benzyloxy-propyl)-cyclopropanesulfonic acid [7-(2-fluoro-4-iodo-phenylamino)-6-methyl-5-oxo-2,3-dihydro-5H-oxazolo[3,2-a]pyridin-8-yl]-amideYield 28.2%

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: 0.5 g, 1.246 mmol) in pyridine (5 ml) was reacted with 1-(3-benzyloxy-propyl)-cyclopropanesulfonyl chloride (0.39 mg, 1.371 mmol) to afford the crude product. Purification by column chromatography on silica gel (2% MeOH in CHCl3) afforded 0.23 g of the product (28% yield). LCMS: 93.01%, m/z=654.0 (M+1). HPLC: 74.6%

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-8a0061d09d394a8c831ec0d587222afd
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

Loading…