5-Methoxyindoleacetic acid → HCID 178488078, compound

HRID 1819697Notes

Reaction equation

HRID 1819697 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]([NH2:26])=[N:11][C:12](=[O:25])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[NH:16][CH:15]=2)[CH:5]=[C:4]([Cl:27])[C:3]=1[NH:28][C:29](=[O:31])[CH3:30].[CH3:32]OC1C=C2C(=CC=1)NC=C2CC(O)=O.NC1C(C)=CC(CN)=CC=1Cl>>[Cl:27][C:4]1[CH:5]=[C:6]([CH2:8][NH:9][C:10]([NH2:26])=[N:11][C:12](=[O:25])[CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[NH:16][CH:15]=2)[CH:7]=[C:2]([CH3:32])[C:3]=1[NH:28][C:29](=[O:31])[CH3:30]

Participants

4

Reactant 3

HCID 189865-Methoxyindoleacetic acidHCID 552557664-(Aminomethyl)-2-chloro-6-methylanilineHCID 178488081HCID 178488081, compound

Product 1

HCID 178488078HCID 178488078, compound

Procedure

In a manner similar to that used in the preparation of the compound of example 2, but using 2-(5-methoxy-1H-indol-3-yl)acetic acid in step 9 (A) and 4-amino-3-chloro-5-methylbenzylamine (preparation G) in step 9 (B), the title compound was prepared. MS (ESI) (M+H)+=442.04 1H-NMR (500 MHz, CD3OD) δ 7.20-7.39 (m, 3 H), 7.16 (s, 1 H), 7.05 (d, J=2.14 Hz, 1 H), 6.82 (dd, J=8.55, 2.44 Hz, 1 H), 4.46 (s, 2 H), 3.93 (s, 2 H), 3.82 (s, 3 H), 2.24 (s, 3 H), 2.18 (s, 3 H).

Sources & evidence

ORD record
ord-35a7fd84531e48afa8d402dab7d60363
Source dataset
uspto-grants-2009_10
Patent number
US07601751B2

Reaction notes

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