HCID 58380528, compound → HCID 52934328, compound

HRID 1259414Notes

Reaction equation

HRID 1259414 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.[O:22]1[CH2:25][CH:24]([CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29])[CH2:23]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][CH2:26][CH:24]2[CH2:25][O:22][CH2:23]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 58380528HCID 58380528, compoundHCID 866563352-(Oxetan-3-yl)ethanesulfonyl chloride

Product 1

HCID 52934328HCID 52934328, compoundYield 9%

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, 0.673 mmol) was reacted with 2-(oxetan-3-yl)ethanesulfonyl chloride (0.18 g, 1.009 mmol) in dry pyridine (3 mL) to afford the crude product. Purification by preparative HPLC, followed by flash column chromatography (3% methanol in chloroform) afforded 20 mg of the compound (17A) (9% yield) and 3 mg of the hydrolyzed by-product (compound (17B).

Workup

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

Sources & evidence

ORD record
ord-cb9ab4f798954eb9915b982d8b790ba4
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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