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

HRID 874202Notes

Reaction equation

HRID 874202 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](O)=[O:20])=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][NH:29][CH2:30][CH2:31][O:32][CH3:33]>>[ClH:1].[CH3:33][O:32][CH2:31][CH2:30][N:29]([CH2:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=1)[C:19](=[O:20])[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 4723821(2-Methoxyethyl)((pyridin-2-yl)methyl)amineHCID 185457132-(4-Chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid

Product 1

HCID 56591522N-(2-methoxyethyl)-N-(2-pyridinylmethyl)-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 46%

Procedure

According to the method of Example 14, 2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-(2-pyridinylmethyl)-2-methoxyethylamine were used as raw materials for synthesis, white solid powder, yield 46.0%. m.p. 238-239° C., ESI-MS m/z: 450[M+H]+, 1H NMR(D2O, 400 MHz)δ: 2.37(s, 2.5H), 2.39(s, 0.5H), 3.10(s, 0.5H), 3.14(s, 2.5H), 3.52(t, 2H, J=4.76 Hz) 3.74(t, 2H, J=4.76 Hz), 4.15(s, 0.4H), 4.41(s, 1.6H), 4.76(s, 1.6H), 4.85(s, 0.4H), 7.15-7.23(m, 1H), 7.30-7.47(m, 4H), 7.50(s, 1H), 7.60-7.70(m, 2H), 8.09-8.11(m, 1H), 8.25-8.45(m, 2H).

Workup

  1. customwere used as raw materials for synthesis, white solid powder, yield 46.0%

Sources & evidence

ORD record
ord-c0f939b35dc3401680807fcbf55e9cc9
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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