5-Chloro-2-methoxybenzene-1-sulfonyl chloride → HCID 68697511, compound

HRID 2235120Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:32][CH3:33])=[C:6]([S:8]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]([NH:22][C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)=[O:21])[CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.Cl[C:35]1C=CC(OC)=C(S(Cl)(=O)=O)[CH:40]=1>>[CH2:35]([O:28][C:27](=[O:29])[C:26]1[CH:30]=[CH:31][C:23]([NH:22][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][N:11]3[S:8]([C:6]3[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[O:32][CH3:33])(=[O:10])=[O:9])=[CH:15][CH:16]=2)=[O:21])=[CH:24][CH:25]=1)[CH3:40]

Participants

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chloride

HCID 15984085HCID 15984085, compound

Product 1

HCID 68697511HCID 68697511, compound

Procedure

4-{[1-(5-Chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=485.2 (M−H), was prepared in analogy to example 30, steps 1 to 6. Step 5 was performed using 5-chloro-2-methoxy-benzenesulfonyl chloride, yielding 4-{[1-(5-chloro-2-methoxy-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-0facf3fce6c54982b0e6fd026f9567cd
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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