2-Methoxyethylamine → HCID 135497052, compound

HRID 2245565Notes

Reaction equation

HRID 2245565 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([O:20]C)=O)[CH:16]=3)[NH:11][C:10]=2[OH:22])[CH:4]=1)#[N:2].[CH3:23][O:24][CH2:25][CH2:26][NH2:27]>>[C:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([NH:27][CH2:26][CH2:25][O:24][CH3:23])=[O:20])[CH:16]=3)[NH:11][C:10]=2[OH:22])[CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 80182-MethoxyethylamineHCID 136379976HCID 136379976, compound

Product 1

HCID 135497052HCID 135497052, compoundYield 8%

Procedure

Starting material: methyl 3-(4-cyanopyridin-2-yl)-2-hydroxy-1H-indole-5-carboxylate and 2-methoxyethanamine. The product was purified on a silica gel column using chloroform/methanol/aqueous NH3, (150:10:1), as the eluent. The combined fractions were concentrated, stirred for 2 h in ethyl acetate (5 mL), and the formed precipitate was filtered off to give 0.012 g (8% yield) of the title compound as a dark-red powder: 1H NMR (DMSO-d6, 300 MHz) δ 14.67 (br s, 1H), 10.83 (s, 1H), 8.46 (br s, 1H), 8.16 (d, J=6.3 Hz, 1H), 7.98 (s, 1H), 7.81 (s, 1H), 7.56 (d, J=7.8 Hz, 1H), 6.95 (d, J=7.8 Hz, 1H), 6.86 (d, J=6.3 Hz, 1H), 3.48 (br s, 4H), 3.31 (s, 3H); MS (ES) m/z 337 (M++1).

Workup

  1. customThe product was purified on a silica gel column
  2. concentrationThe combined fractions were concentrated
  3. filtrationthe formed precipitate was filtered off

Sources & evidence

ORD record
ord-32b46821299f434fb2b448db2b839ceb
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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