3-Amino-1-propanol → 6-Methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

HRID 985257Notes

Reaction equation

HRID 985257 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].[OH:17][CH2:18][CH2:19][CH2:20][NH2:21].C(Cl)(=O)C(Cl)=O.CNC(C1C2C(=CC(OC)=CC=2)N(C)C=1C)=O>>[OH:17][CH2:18][CH2:19][CH2:20][NH:21][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]

Participants

5

Reactant 4

HCID 90863-Amino-1-propanolHCID 65578Oxalyl chlorideHCID 207678696-methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid methylamideHCID 221434941,2-dimethyl-6-methoxy1H-indole-3-carboxylic acid

Product 1

HCID 207679016-Methoxy-1,2-dimethyl-1H-indole-3-carboxylic acid (3-hydroxy-propyl)-amide

Procedure

This material was prepared by the reaction of 1,2-dimethyl-6-methoxy-1H-indole-3-carboxylic acid 16c with 3-hydroxy-propyl amine and oxalyl chloride in a manner as previously described for 16d. 1H NMR (300 MHz, CD3OD) δ7.52 (1H, d, J=8.6 Hz), 6.73 (1H, d, J=2.1 Hz), 6.68 (1H, dd, J=2.1, 8.6 Hz), 3.69 (2H, t, J=6.1 Hz), 3.79 (3H, s), 3.63 (3H, s), 3.51 (2H, m), 2.57 (3H, s), 1.85 (2H, m). LCMS (ESI+) [M+H]/z Calc'd 291, found 291.

Sources & evidence

ORD record
ord-9d1c42e70eec4e0ea12c2aa57d037663
Source dataset
uspto-grants-2005_03
Patent number
US06869962B2

Reaction notes

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