Dichloromethane → 6-Methoxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamide

HRID 985266Notes

Reaction equation

HRID 985266 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([C:13]([OH:15])=O)=[C:3]1[CH3:16].C(Cl)(=O)C(Cl)=O.C(Cl)Cl.[N:26]1([CH2:32][CH2:33][CH2:34][NH2:35])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>>[CH3:12][O:11][C:8]1[CH:9]=[C:10]2[C:5]([C:4]([C:13]([NH:35][CH2:34][CH2:33][CH2:32][N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:15])=[C:3]([CH3:16])[N:2]2[CH3:1])=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 61055N-(3-Aminopropyl)morpholineHCID 65578Oxalyl chlorideHCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 221435776-Methoxy-1,2-dimethyl-N-(3-morpholin-4-ylpropyl)-1H-indole-3-carboxamideYield 59%

Procedure

This material was prepared from 6-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid 16c (0.483 g, 2.20 mmole) with 2.0 M oxalyl chloride in CH2Cl2 (2.2 ml, 4.4 mmole) and 3-morpholin-4-ylpropylamine in a manner as previously described for example 16d to give a white solid (0.445 g, 59%). 1H NMR (300 MHz, CDCl3) δ7.60 (1H, d, J=8.6 Hz), 6.82 (1H, dd, J=2.3, 8.6 Hz), 6.77 (1H, d, J=2.3 Hz), 6.71 (1H, s), 3.87 (3H, s), 3.62 (3H, s), 3.57 (6H, m), 2.69 (3H, s), 2.50 (2H, t, J=6.6 Hz), 2.43 (4H, m), 1.81 (2H, m); ESIMS (MH+): 346.20.

Sources & evidence

ORD record
ord-3e0a66e912424a9ea001c550aadf430e
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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