5-Fluoro-2-methylbenzenesulphonyl chloride → HCID 66789360, compound

HRID 1660819Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][CH2:20][N:19]([S:23]([C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=4[CH3:33])(=[O:25])=[O:24])[C:18]=3[CH:34]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].F[C:36]1C=CC(C)=C(S(Cl)(=O)=O)[CH:41]=1>>[CH2:36]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][CH2:20][N:19]([S:23]([C:26]4[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=4[CH3:33])(=[O:25])=[O:24])[C:18]=3[CH:34]=2)=[O:13])=[CH:10][C:2]=1[F:1])[CH3:41]

Participants

Reactant 2

HCID 1362865-Fluoro-2-methylbenzenesulphonyl chloride

HCID 24762710HCID 24762710, compound

Product 1

HCID 66789360HCID 66789360, compound

Procedure

2-Fluoro-4-{[4-(5-fluoro-2-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=487.1 (M−H), was prepared as described for example 21, steps 1 to 8. Step 7 was performed using 5-fluoro-2-methyl-benzenesulfonyl chloride and yielded 2-fluoro-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-7232235e28434373af605a850da5d874
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030308B2

Reaction notes

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