(2-Methoxyethyl)(pyridin-3-ylmethyl)amine → N-(2-methoxyethyl)-N-(3-pyridinylmethyl)-2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochloride

HRID 874208Notes

Reaction equation

HRID 874208 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]3[C:18]=2[CH2:19][C:20](O)=[O:21])[CH:5]=[CH:6][C:7]=1[Cl:8].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][NH:30][CH2:31][CH2:32][O:33][CH3:34])[CH:24]=1>>[ClH:1].[CH3:34][O:33][CH2:32][CH2:31][N:30]([CH2:29][C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=1)[C:20](=[O:21])[CH2:19][C:18]1[N:12]2[CH:13]=[CH:14][C:15]([CH3:17])=[CH:16][C:11]2=[N:10][C:9]=1[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

3

Reactant 2

HCID 4720010(2-Methoxyethyl)(pyridin-3-ylmethyl)amineHCID 89521808HCID 89521808, compound

Product 1

HCID 56591622N-(2-methoxyethyl)-N-(3-pyridinylmethyl)-2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 74.4%

Procedure

According to the method of Example 14, 2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-(3-pyridinylmethyl)-2-methoxyethylamine were used as raw materials for synthesis, to obtain white solid powder, yield 74.4%. m.p. 235-237° C., ESI-MS m/z: 484[M+H]+, 1H NMR(DMSO-d6, 400 MHz)δ: 2.58(s, 3H), 3.20(s, 0.3H), 3.26(s, 2.7H), 3.57(t, 2H, J=4.76 Hz), 3.76(t, 2H, J=4.76 Hz), 4.43(s, 0.2H), 4.62(s, 1.8H), 4.74(s, 1.8H), 4.97(s, 0.2H), 7.47-7.48(d, 1H, J=7.00 Hz), 7.61(dd, 1H, J=8.4 Hz, 2.24 Hz), 7.8(s, 1H), 7.87-7.88(m, 1H), 7.91-7.92(d, 1H, J=2.24 Hz), 7.95-7.97(d, 1H, J=8.40 Hz), 8.27-8.29(m, 1H), 8.66-8.68(d, 1H, J=7.00 Hz), 8.75-8.79(m, 2H).

Workup

  1. customwere used as raw materials for synthesis
  2. customto obtain white solid powder, yield 74.4%

Sources & evidence

ORD record
ord-bc12070a787d4d1388f95fc44e9d0a8a
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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