3-Cyanobenzene-1-sulfonyl chloride → HCID 66788894, compound

HRID 641303Notes

Reaction equation

[C:1]([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])=[C:28]([F:35])[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)(=O)[NH2:2].[C:36]([C:38]1C=C(S(Cl)(=O)=O)C=CC=1)#N>>[CH2:36]([O:32][C:30](=[O:31])[C:29]1[CH:33]=[CH:34][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]([C:1]#[N:2])[CH:5]=4)(=[O:11])=[O:12])[C:18]=3[CH:19]=2)=[O:24])=[CH:27][C:28]=1[F:35])[CH3:38]

Participants

Reactant 2

HCID 28013603-Cyanobenzene-1-sulfonyl chloride

HCID 24762802HCID 24762802, compound

Product 1

HCID 66788894HCID 66788894, compound

Procedure

4-{[4-(3-Carbamoyl-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-2-fluoro-benzoic acid, MS (ISP): m/e=500.0 (M+H+.), was prepared as described for example 21, steps 1 to 8. Step 7 was performed using 3-cyano-benzenesulfonyl chloride and yielded 4-{[4-(3-cyano-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-2-fluoro-benzoic acid ethyl ester, which was hydrolyzed in step 8 at both the carboxylic acid ester and the cyano position.

Sources & evidence

ORD record: ord-06c9c9c1e7dc4e50bec9faf661281c65
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696200B2

Reaction notes

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