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

HRID 874204Notes

Reaction equation

HRID 874204 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][CH3:32]>>[ClH:1].[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)[CH3:32]

Participants

3

Reactant 2

HCID 4723804N-(pyridin-2-ylmethyl)ethanamineHCID 89521808HCID 89521808, compound

Product 1

HCID 56591614N-ethyl-N-(2-pyridinylmethyl)-2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 75.5%

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)ethylamine were used as raw materials for synthesis, white solid powder, yield 75.5%. m.p. 217-220° C., ESI-MS m/z: 454[M+H]+, 1H NMR(DMSO-d6, 400 MHz)δ: 0.99(t, 1.5H, J=7.00 Hz), 1.25(t, 1.5H, J=7.00 Hz), 2.57(s, 1.5H), 2.60(s, 1.5H), 3.33(q, 1H, J=7.00 Hz), 3.65(q, 1H, J=7.00 Hz), 4.56(s, 1H), 4.59(s, 1H), 4.78(s, 1H), 4.86(s, 1H), 7.40-7.53(m, 1H), 7.54-7.68(m, 2H), 7.78-7.81(m, 1H), 7.89(s, 1H), 7.91-7.95(m, 1H), 8.62-8.67(m, 2H), 8.84-8.86(m, 2H).

Workup

  1. customwere used as raw materials for synthesis, white solid powder, yield 75.5%

Sources & evidence

ORD record
ord-fb521ce08a45442888047aacd17c4350
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

Loading…