Benzocaine → HCID 68699655, compound

HRID 2235115Notes

Reaction equation

ClC1C=C(S([N:11]2[C:19]3[C:14](=[C:15]([O:32][CH3:33])[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)=O)C=CC=1.[CH2:34](OC(=O)C1C=CC(N)=CC=1)[CH3:35]>>[CH2:34]([O:29][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([NH:22][C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH2:13][CH2:12][NH:11]3)=[C:15]([O:32][CH3:33])[CH:16]=2)=[O:21])=[CH:31][CH:30]=1)[CH3:35]

Participants

Reactant 2

HCID 2337Benzocaine

HCID 16051861HCID 16051861, compound

Product 1

HCID 68699655HCID 68699655, compound

Procedure

4-{[1-(3-Chloro-benzenesulfonyl)-4-methoxy-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, m/z (ES+): 487.29 (M+H+.), was prepared in analogy to example 14, steps 1 to 6. Step 4 was performed using 4-amino-benzoic acid ethyl ester, yielding 4-[(4-methoxy-2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester. This was reacted with 3-chloro-benzenesulfonyl chloride in step 5, yielding 4-{[1-(3-chloro-benzenesulfonyl)-4-methoxy-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid ethyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-638907930de6422b9912f88240584184
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713996B2

Reaction notes

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