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

HRID 874207Notes

Reaction equation

HRID 874207 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]([OH:22])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH2:29][NH:30][CH2:31][CH2:32][O:33][CH3:34]>>[ClH:1].[CH3:34][O:33][CH2:32][CH2:31][N:30]([CH2:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)[C:20](=[O:22])[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 4723821(2-Methoxyethyl)((pyridin-2-yl)methyl)amineHCID 89521808HCID 89521808, compound

Product 1

HCID 56591620N-(2-methoxyethyl)-N-(2-pyridinylmethyl)-2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 68.6%

Procedure

According to the method of Example 14, 2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-(2-pyridinylmethyl)-2-methoxyethylamine were used as raw materials for synthesis, to obtain light yellow solid powder, yield 68.6%. m.p. 236-238° C., ESI-MS m/z: 484[M+H]+, 1H NMR(DMSO-d6, 400 MHz)δ: 2.57(s, 2H), 2.60(s, 1H), 3.16(s, 1H), 3.27(s, 2H), 3.40(t, 0.7H, J=4.76 Hz), 3.47(t, 0.7H, J=4.76 Hz), 3.60(t, 1.3H, J=4.76 Hz), 3.84(t, 1.3H, J=4.76 Hz), 4.56(s, 0.7H), 4.66(s, 1.3H), 4.84(s, 1.3H), 4.93(s, 0.7H), 7.43-7.50(m, 1H), 7.62-7.65(dd, 1H, J=8.40 Hz, 2.24 Hz), 7.69-7.81(m, 2H), 7.88-7.90(d, 1H, J=8.40 Hz), 7.92-7.93(d, 1H, J=2.24 Hz), 7.95(s, 1H), 8.62-8.78(m, 2H), 8.76-8.84(m, 1H).

Workup

  1. customwere used as raw materials for synthesis
  2. customto obtain light yellow solid powder, yield 68.6%

Sources & evidence

ORD record
ord-f882826ce4f6422d9c230d32184b6a14
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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