2-Methoxyethylamine → HCID 66780409, compound

HRID 1470346Notes

Reaction equation

HRID 1470346 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[O:21][C:20]3[C:15](=[N:16][CH:17]=[CH:18][C:19]=3[C:22]3[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=3)[C:25]([OH:27])=O)[CH:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:31][O:32][CH2:33][CH2:34][NH2:35]>>[CH3:31][O:32][CH2:33][CH2:34][NH:35][C:25](=[O:27])[C:24]1[CH:28]=[CH:29][CH:30]=[C:22]([C:19]2[CH:18]=[CH:17][N:16]=[C:15]3[CH:14]=[C:13]([C:5]4[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)[O:21][C:20]=23)[CH:23]=1

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 66779501HCID 66779501, compound

Product 1

HCID 66780409HCID 66780409, compoundYield 62%

Procedure

Starting from 3-[2-(3,4,5-trimethoxyphenyl)furo[3,2-b]pyridin-7-yl]benzoic acid (0.062 mmol) and 2-methoxyethylamin (0.069 mmol) the product is prepared analogously to “A43” and obtained as colorless solid in a yield of 62%. HPLC (method A): Rt 2.53 min (purity 98.8%); LCMS (ESI+) (method E): Rt 1.78 min, M+H+ 463.2 m/z; 1H NMR (500 MHz, DMSO-d6) δ [ppm] 8.84 (s, 1H), 8.79-8.72 (m, 1H), 8.60 (d, J=5.1, 1H), 8.28 (d, J=8.3, 1H), 8.03 (d, J=7.9, 1H), 7.78 (s, 1H), 7.75-7.70 (m, 2H), 7.35 (d, J=16.3, 2H), 3.93 (s, 6H), 3.74 (s, 3H), 3.54-3.43 (m, 4H), 3.28 (s, 3H).

Workup

  1. customis prepared analogously to “A43”
  2. customobtained as colorless solid in a yield of 62%

Sources & evidence

ORD record
ord-9a30d6232bec468e955a29d5382ca404
Source dataset
uspto-grants-2015_04
Patent number
US09006440B2

Reaction notes

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