5-Fluoro-2-methylbenzenesulphonyl chloride → HCID 66969435, compound

HRID 641292Notes

Reaction equation

HRID 641292 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:33])=[C:6]([S:8]([N:11]2[C:16]3[CH:17]=[C:18]([C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.F[C:35]1C=CC(C)=C(S(Cl)(=O)=O)[CH:40]=1>>[CH2:35]([O:29][C:28](=[O:30])[C:27]1[CH:26]=[CH:25][C:24]([NH:23][C:21]([C:18]2[CH:19]=[CH:20][C:15]3[O:14][CH2:13][CH2:12][N:11]([S:8]([C:6]4[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[CH3:33])(=[O:9])=[O:10])[C:16]=3[CH:17]=2)=[O:22])=[CH:32][CH:31]=1)[CH3:40]

Participants

3

Reactant 2

HCID 1362865-Fluoro-2-methylbenzenesulphonyl chlorideHCID 46213773HCID 46213773, compound

Product 1

HCID 66969435HCID 66969435, compound

Procedure

4-{[4-(5-Fluoro-2-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=468.9 (M−H), was prepared as described for example 14, steps 1 to 8. Step 7 was performed using 5-fluoro-2-methyl-benzenesulfonyl chloride and yielded 4-{[4-(5-fluoro-2-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 8.

Sources & evidence

ORD record
ord-b8e65fb0ab884043800c2ab9133c9961
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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