Methylamine → HCID 20767782, compound

HRID 1825154Notes

Reaction equation

HRID 1825154 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14](O)=[O:15])=[C:4]1[CH3:17])[CH3:2].C(Cl)(=O)C(Cl)=O.[CH3:24][NH2:25]>>[CH3:24][NH:25][C:14]([C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]=1[CH3:17])=[O:15]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 65578Oxalyl chlorideHCID 22143615HCID 22143615, compound

Product 1

HCID 20767782HCID 20767782, compoundYield 95%

Procedure

This material was prepared from the reaction of 1-ethyl-6-methoxy-2-methyl-1H-indole-3-carboxylic acid 71c (350 mg, 1.5 mmole), oxalyl chloride (1.1 ml, 2.0M solution) and methylamine (1.5 ml, 2.0M solution) in a manner as previously described for example 16d to give 350 mg product as beige solid (95% yield). 1H NMR (300 MHz, CDCl3) δ 7.56 (1H, d, J=8.7 Hz), 6.84 (1H, dd, J=2.3, 8.7 Hz), 6.80 (1H, d, J=2.3 Hz), 5.84 (1H, bs), 4.10 (2H, q, J=7.2 Hz), 3.87 (3H, s), 3.03 (3H, d, J=4.9 Hz), 2.70 (3H, s), 1.33 (3H, t, J=7.2 Hz).

Sources & evidence

ORD record
ord-40a2ccab93b746609604e79dc64a1889
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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