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

HRID 874205Notes

Reaction equation

HRID 874205 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]=[C:25]([CH2:29][NH:30][CH2:31][CH3:32])[CH:24]=1>>[ClH:1].[CH2:31]([N:30]([CH2:29][C:25]1[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=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 4716480Ethyl[(pyridin-3-yl)methyl]amineHCID 89521808HCID 89521808, compound

Product 1

HCID 56591616N-ethyl-N-(3-pyridinylmethyl)-2-(3,4-dichlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 70.8%

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)ethylamine were used as raw materials for synthesis, to obtain white solid powder, yield 70.8%. m.p. 245-248° C., ESI-MS m/z: 454[M+H]+, 1H NMR(DMSO-d6, 400 MHz)δ: 1.06(t, 0.7H, J=7.00 Hz), 1.25(t, 2.3H, J=7.00 Hz), 2.58(s, 3H), 3.34(q, 0.5H, J=7.00 Hz), 3.58(q, 1.5H, J=7.00 Hz), 4.45(s, 0.5H), 4.57(s, 1.5H), 4.70(s, 1.5H), 4.92(s, 0.5H), 7.44-7.47(d, 1H, J=7.00 Hz), 7.56(dd, 0.2H, J=8.40 Hz, 1.96 Hz), 7.63(dd, 0.8H, J=8.40 Hz, 2.24 Hz), 7.80(s, 1H), 7.86(d, 0.2H, J=2.24 Hz), 7.87(d, 0.8H, J=1.96 Hz), 7.90(m, 1H), 7.94(d, 1H, J=8.40 Hz), 8.30-8.31(m, 1H), 8.74-8.77(m, 1H), 8.79(d, 1H, J=7.00 Hz), 8.82(m, 1H).

Workup

  1. customwere used as raw materials for synthesis
  2. customto obtain white solid powder, yield 70.8%

Sources & evidence

ORD record
ord-712f0851daca494d98a66ea3bda2bced
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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