Benzocaine → HCID 68696720, compound

HRID 2235119

Reaction equation

HRID 2235119 reaction equation
ClC1C=C(S([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=4)=[O:22])[CH:19]=3)[CH2:14][CH2:13]2)(=O)=O)C=C(Cl)C=1.CO[C:35]([C:37]1C=C2C(C=CN2)=CC=1)=O.COC(C1C=C2C(CCN2)=CC=1)=O.COC(C1C=C2C(CCN2C(OC(C)(C)C)=O)=CC=1)=O.C(OC(N1C2C(=CC=C(C(O)=O)C=2)CC1)=O)(C)(C)C.C(OC(=O)C1C=CC(N)=CC=1)C>>[CH2:35]([O:30][C:28](=[O:29])[C:27]1[CH:26]=[CH:25][C:24]([NH:23][C:21]([C:18]2[CH:19]=[C:20]3[C:15]([CH2:14][CH2:13][NH:12]3)=[CH:16][CH:17]=2)=[O:22])=[CH:32][CH:31]=1)[CH3:37]

Participants

7

Reactant 6

HCID 2337BenzocaineHCID 639844Methyl indole-6-carboxylateHCID 16051865HCID 16051865, compoundHCID 16244446Methyl 2,3-dihydro-1H-indole-6-carboxylateHCID 183548491H-INDOLE-1,6-DICARBOXYLIC ACID,2,3-DIHYDRO-,1-(1,1-DIMETHYLETHYL)ESTERHCID 665750481-tert-butyl 6-methyl 2,3-dihydro-1H-indole-1,6-dicarboxylate

Product 1

HCID 68696720HCID 68696720, compound

Procedure

4-{[1-(3,5-Dichloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=488.9 (M−H), was prepared in analogy to example 14, steps 1 to 6. Step 1 was performed starting from 1H-indole-6-carboxylic acid methyl ester, which was reduced to 2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (see also example 34). This was protected in step 2 to 2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester, which was then hydrolyzed to 2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester in step 3. Step 4 was performed using 4-amino-benzoic acid ethyl ester, yielding 4-[(2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid ethyl ester. This was reacted with 3,5-dichloro-benzenesulfonyl chloride in step 5, yielding 4-{[1-(3,5-dichloro-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, which was hydrolyzed in step 6.

Sources & evidence

ORD record
ord-996da454903e4198938d665a92b005cb
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Linked notes

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