Propylamine → 6-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

HRID 985252Notes

Reaction equation

HRID 985252 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].S(Cl)(Cl)=O.[CH2:21]([NH2:24])[CH2:22][CH3:23]>>[CH2:21]([NH:24][C:13]([C:4]1[C:5]2[C:10](=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=2)[N:2]([CH3:1])[C:3]=1[CH3:16])=[O:15])[CH2:22][CH3:23]

Participants

4

Reactant 3

HCID 7852PropylamineHCID 24386Thionyl ChlorideHCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 207678686-Methoxy-1,2-dimethyl-1H-indol-3-carboxylic acid propylamide

Procedure

This material was prepared from 1,2-dimethyl-6-methoxy-1H-indole-3-carboxylic acid 16c, thionyl chloride and propylamine in a manner as previously described for example 9d. 1H NMR (300 MHz, CDCl3) δ7.55 (1H, d, J=8.6 Hz), 6.84 (1H, dd, J=2.2, 8.6 Hz), 6.78 (1H, d, J=2.2 Hz), 5.87 (1H, bs), 3.87 (3H, s), 3.63 (3H, s), 3.45 (2H, m), 2.69 (3H, s), 1.67 (2H, m), 1.02 (3H, t, J=7.4 Hz). LCMS (ESI+) [M+H]/z Calc'd 261, found 261.

Sources & evidence

ORD record
ord-5e67f6119fef4d369b4b17592aa05478
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

Loading…