Methyl 4-Amino-2-chlorobenzoate → HCID 68702077, compound

HRID 2235110Notes

Reaction equation

HRID 2235110 reaction equation
[Cl: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]3S(C3C=CC=C(C(F)(F)F)C=3)(=O)=O)=[C:16]([O:36][CH3:37])[CH:15]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:38]OC(=O)C1C=CC(N)=CC=1Cl>>[CH3:38][O:6][C:4](=[O:5])[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][NH:20]3)=[C:16]([O:36][CH3:37])[CH:15]=2)=[O:13])=[CH:10][C:2]=1[Cl:1]

Participants

3

Reactant 2

HCID 11839197Methyl 4-Amino-2-chlorobenzoateHCID 16051765HCID 16051765, compound

Product 1

HCID 68702077HCID 68702077, compound

Procedure

2-Chloro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid, m/z (ES+): 555.3 (M+H+.), was prepared in analogy to example 14, steps 1 to 6. Step 4 was performed using 4-amino-2-chlorobenzoic acid methyl ester, yielding 2-chloro-4-[(4-methoxy-2,3-dihydro-1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester. This was reacted with 3-trifluoromethyl-benzenesulfonyl chloride in step 5, yielding 2-chloro-4-{[4-methoxy-1-(3-trifluoromethyl-benzenesulfonyl)-2,3-dihydro-1H-indole-6-carbonyl]-amino}-benzoic acid methyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record
ord-5f9d6a098e4f4511a8bdd5ee679ca00c
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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