3-Amino-5-methylisoxazole → HCID 22614977, compound

HRID 843172Notes

Reaction equation

HRID 843172 reaction equation
[CH3:1][C:2]1[C:6]2[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=3)=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:24]=O.[NH2:26][C:27]1[CH:31]=[C:30]([CH3:32])[O:29][N:28]=1>C1(C)C=CC=CC=1>[CH3:32][C:30]1[O:29][N:28]=[C:27]([NH:26][CH2:24][C:3]2[O:4][C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][CH2:13][CH2:14][N:15]([CH3:23])[CH2:16][C:17]4[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=4)[C:6]=3[C:2]=2[CH3:1])[CH:31]=1

Participants

4

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 22614941HCID 22614941, compound

Product 1

HCID 22614977HCID 22614977, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-methyl-4-[3-(methyl-pyridin-3-ylmethyl-amino)-propoxy]-benzofuran-2-carbaldehyde (55 mg) and 3-amino-5-methylisooxazole (160 mg) in toluene (4 ml) was refluxed overnight. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography developed by ethyl acetate and methanol to give the titled compound as a pale yellow oil (46 mg). ESI-MS: m/z 419 (MH+); 1H-NMR (CDCl3): δ 2.00-2.09 (2H, m), 2.29 (3H, s), 2.44 (3H, s), 2.48 (2H, s), 2.68 (2H, t, J=10.2 Hz), 3.53 (2H, s), 4.14 (2H, t, J=5.9 Hz), 6.16 (1H, s), 6.62 (1H, d, J=7.9 Hz), 7.05-7.17 (2H, m), 7.32 (1H, s), J=7.9 Hz), 7.59-7.63 (1H, m), 8.41 (1H, dd, J=1.7 Hz, 4.9 Hz), 8.51 (1H, d, J=2.0 Hz), 8.82 (1H, s).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7894d8a2712443db93e0161e0b4f174
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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