3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 66789933, compound

HRID 641297Notes

Reaction equation

COC(=O)C1C=CC(NC(=O)C2C=CC(O)=C(N)C=2)=CC=1F.[CH2:23]([O:25][C:26](=[O:47])[C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]2[CH:37]=[CH:38][C:39]3[O:44][CH2:43][CH2:42][NH:41][C:40]=3[CH:45]=2)=[O:35])=[CH:29][C:28]=1[F:46])[CH3:24].[F:48][C:49]([F:61])([F:60])[C:50]1[CH:51]=[C:52]([S:56](Cl)(=[O:58])=[O:57])[CH:53]=[CH:54][CH:55]=1>>[CH2:23]([O:25][C:26](=[O:47])[C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]([C:36]2[CH:37]=[CH:38][C:39]3[O:44][CH2:43][CH2:42][N:41]([S:56]([C:52]4[CH:53]=[CH:54][CH:55]=[C:50]([C:49]([F:48])([F:60])[F:61])[CH:51]=4)(=[O:58])=[O:57])[C:40]=3[CH:45]=2)=[O:35])=[CH:29][C:28]=1[F:46])[CH3:24]

Participants

Reactant 3

HCID 27332503-(Trifluoromethyl)benzenesulfonyl chloride

HCID 66788850HCID 66788850, compound

HCID 66789221HCID 66789221, compound

Product 1

HCID 66789933HCID 66789933, compound

Procedure

2-Fluoro-4-{[4-(3-trifluoromethyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=523.0 (M−H), was prepared as described for example 14, steps 1 to 8. Step 4 was performed using 4-amino-2-fluoro-benzoic acid ethyl ester, yielding 4-(4-benzyloxy-3-nitro-benzoylamino)-2-fluoro-benzoic acid ethyl ester, which was reduced to 4-(3-amino-4-hydroxy-benzoylamino)-2-fluoro-benzoic acid methyl ester in step 5 and cyclized to 4-[(3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl)-amino]-2-fluoro-benzoic acid ethyl ester in step 6. Step 7 was performed using 3-trifluoromethyl-benzenesulfonyl chloride and yielded 2-fluoro-4-{[4-(3-trifluoromethyl-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-d8efb2e8c6ce45b78ca352e69670948f
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696200B2

Reaction notes

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