6-Methoxy-m-toluenesulfonyl chloride → HCID 68700696, compound

HRID 2235109Notes

Reaction equation

[F:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[C:16]([O:35][CH3:36])[CH:15]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO[C:39]1C=CC(C)=C[C:40]=1S(Cl)(=O)=O>>[CH2:39]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]2[CH:22]=[C:21]3[C:17]([CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[C:16]([O:35][CH3:36])[CH:15]=2)=[O:13])=[CH:10][C:2]=1[F:1])[CH3:40]

Participants

Reactant 2

HCID 1451496-Methoxy-m-toluenesulfonyl chloride

HCID 16051764HCID 16051764, compound

Product 1

HCID 68700696HCID 68700696, compound

Procedure

2-Fluoro-4-{[4-methoxy-1-(2-methoxy-5-methyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, m/z (ES+): 515.37 (M+H+.), was prepared in analogy to example 14, steps 1 to 6. Step 5 was performed using 2-methoxy-5-methyl-benzenesulfonyl chloride and yielded 2-fluoro-4-{[4-methoxy-1-(2-methoxy-5-methyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-40fd1c80890845e1b59f265b6a12067e
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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