3-Amino-1-propanol → N-(3-hydroxypropyl)-1H-indole-2-carboxamide

HRID 2378355Notes

Reaction equation

HRID 2378355 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.[NH2:13][CH2:14][CH2:15][CH2:16][OH:17]>>[OH:17][CH2:16][CH2:15][CH2:14][NH:13][C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:12]

Participants

3

Reactant 2

HCID 90863-Amino-1-propanolHCID 72899Indole-2-carboxylic acid

Product 1

HCID 2219271N-(3-hydroxypropyl)-1H-indole-2-carboxamideYield 80%

Procedure

1H Indole-2-carboxylic acid (5.0 g, 31 mmol) and 3-amino-1-propanol (2.2 ml, 40.3 mmol) were coupled according to the procedure of Example 17 to 5.46 g (80% yield) of an off-white solid. MP 152-156° C.; 1H NMR (DMSO-d6): δ 1.6-1.7 (m, CH2), 3.31-3.37 (q, CH2), 3.41-3.51 (q, CH2), 4.52 (t, NH), 7.0-7.19 (m, 3 Ar H), 7.40 (d, 1 Ar H), 7.58 (d, 1 Ar H), 8.46 (t, NH), 11.9 (s, NH) Electrospray Mass Spec: m/z 217.2 (M+H)+.

Sources & evidence

ORD record
ord-a972638429e24361bd267ea31f10db31
Source dataset
uspto-grants-2008_12
Patent number
US07470794B2

Reaction notes

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