Ethyl 4-Amino-2-fluorobenzoate → 2-fluoro-4-{[4-(2-methoxy-5-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester

HRID 1360312Notes

Reaction equation

HRID 1360312 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([N:13]1[C:18]2[CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH2:14]1)(=[O:12])=[O:11].[NH2:26][C:27]1[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[C:29]([F:38])[CH:28]=1>>[CH2:34]([O:33][C:31](=[O:32])[C:30]1[CH:36]=[CH:37][C:27]([NH:26][C:23]([C:20]2[CH:21]=[CH:22][C:17]3[O:16][CH2:15][CH2:14][N:13]([S:10]([C:4]4[CH:5]=[C:6]([CH3:9])[CH:7]=[CH:8][C:3]=4[O:2][CH3:1])(=[O:12])=[O:11])[C:18]=3[CH:19]=2)=[O:24])=[CH:28][C:29]=1[F:38])[CH3:35]

Participants

3

Reactant 2

HCID 10797532Ethyl 4-Amino-2-fluorobenzoateHCID 66789677HCID 66789677, compound

Product 1

HCID 667892032-fluoro-4-{[4-(2-methoxy-5-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester

Procedure

The title compound, MS (ISP)=501.1 (M+H)+, was produced as described in example 1, steps 1-6. Step 3 was performed using 2-methoxy-5-methylbenzenesulfonyl chloride, furnishing 4-(2-methoxy-5-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid methyl ester, which was hydrolyzed in step 4, leading to 4-(2-methoxy-5-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carboxylic acid. This was reacted with ethyl 4-amino-2-fluorobenzoate in step 5 and yielded 2-fluoro-4-{[4-(2-methoxy-5-methyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record
ord-cb27a102b317465c9ebd4bc4b26bd331
Source dataset
uspto-grants-2011_02
Patent number
US07879845B2

Reaction notes

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