3-(Difluoromethoxy)benzenesulfonyl chloride → 4-{[4-(3-difluoromethoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester

HRID 641293Notes

Reaction equation

HRID 641293 reaction equation
[F:1][CH:2]([F:35])[O:3][C:4]1[CH:5]=[C:6]([S:10]([N:13]2[C:18]3[CH:19]=[C:20]([C:23]([NH:25][C:26]4[CH:34]=[CH:33][C:29]([C:30]([OH:32])=[O:31])=[CH:28][CH:27]=4)=[O:24])[CH:21]=[CH:22][C:17]=3[O:16][CH2:15][CH2:14]2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.FC(F)O[C:39]1C=C(S(Cl)(=O)=O)C=C[CH:44]=1>>[CH2:39]([O:31][C:30](=[O:32])[C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:23]([C:20]2[CH:21]=[CH:22][C:17]3[O:16][CH2:15][CH2:14][N:13]([S:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH:2]([F:1])[F:35])[CH:5]=4)(=[O:11])=[O:12])[C:18]=3[CH:19]=2)=[O:24])=[CH:34][CH:33]=1)[CH3:44]

Participants

3

Reactant 2

HCID 27782263-(Difluoromethoxy)benzenesulfonyl chlorideHCID 247625534-{[4-(3-Difluoromethoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid

Product 1

HCID 667891534-{[4-(3-difluoromethoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid ethyl ester

Procedure

4-{[4-(3-Difluoromethoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=502.9 (M−H), was prepared as described for example 14, steps 1 to 8. Step 7 was performed using 3-difluoromethoxy-benzenesulfonyl chloride and yielded 4-{[4-(3-difluoromethoxy-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-bcb1ff1b92f145fdb1fa8eab2593f12d
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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