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

HRID 874203Notes

Reaction equation

HRID 874203 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][N:11]3[C:17]=2[CH2:18][C:19]([OH:21])=O)=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][CH2:30][CH2:31][O:32][CH3:33])[CH:23]=1>>[ClH:1].[CH3:33][O:32][CH2:31][CH2:30][N:29]([CH2:28][C:24]1[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=1)[C:19](=[O:21])[CH2:18][C:17]1[N:11]2[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:10]2=[N:9][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 4720010(2-Methoxyethyl)(pyridin-3-ylmethyl)amineHCID 185457132-(4-Chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid

Product 1

HCID 56591524N-(2-methoxyethyl)-N-(3-pyridinylmethyl)-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 69.4%

Procedure

According to the method of Example 14, 2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-(3-pyridinylmethyl)-2-methoxyethylamine were used as raw materials for synthesis, white solid powder, yield 69.4%. m.p. 234-235° C., ESI-MS m/z: 450[M+H]+, 1H NMR(DMSO-d6, 400 MHz) δ: 2.39(s, 2.4H), 2.40(s, 0.6H), 3.10(s, 0.6H), 3.11(s, 2.4H), 3.48(t, 2H, J=4.76 Hz), 3.68(t, 2H, J=4.76 Hz), 4.14(s, 0.4H), 4.38(s, 1.6H), 4.63(s, 1.6H), 4.83(s, 0.4H), 7.16-7.22(m, 1H), 7.34-7.47(m, 4H), 7.51(s, 1H), 7.80-7.82(m, 1H), 8.10-8.12(m, 1H), 8.21-8.27(m, 1H), 8.48-8.51(m, 2H).

Workup

  1. customwere used as raw materials for synthesis, white solid powder, yield 69.4%

Sources & evidence

ORD record
ord-fac2a3f8082a4b8eb67f7c06ed0797ab
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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