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

HRID 874199Notes

Reaction equation

HRID 874199 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][CH3:31].Cl.C(OCC)C>ClCCl>[ClH:1].[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)[CH3:31]

Participants

5

Reactant 3

HCID 4723804N-(pyridin-2-ylmethyl)ethanamineHCID 10953452Ether hydrochlorideHCID 185457132-(4-Chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid

Product 1

HCID 56591516N-ethyl-N-(2-pyridinylmethyl)-2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide.hydrochlorideYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the method of Example 13, 2-(4-chlorophenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-(2-pyridinylmethyl)ethylamine were used as raw materials for synthesis, salified with hydrochloric acid-ethyl ether solution in dry dichloromethane, then crystallized with methanol-tetrahydrofuran to obtain a corresopnding hydrochloride pure product. Yellow solid powder, yield 51.2%. m.p. 178-180° C., ESI-MS m/z: 420[M+H]+, 1H NMR(D2O, 400 MHz)δ: 0.95(t, 0.5H, J=7.00 Hz), 1.14(t, 2.5H, J=7.00 Hz), 2.38(s, 2.5H), 2.40(s, 0.5H), 3.30(q, 0.4H, J=7.00 Hz), 3.56(q, 1.6H, J=7.00 Hz), 4.14(s, 0.4H), 4.36(s, 1.6H), 4.76(s, 1.6H), 4.86(s, 0.4H), 7.14-7.24(m, 1H), 7.30-7.46(m, 4H), 7.50(s, 1H), 7.69-7.75(m, 2H), 8.11-8.13(m, 1H), 8.33-8.53(m, 2H).

Workup

  1. customwere used as raw materials for synthesis
  2. customcrystallized with methanol-tetrahydrofuran

Sources & evidence

ORD record
ord-f7d17342d4924ead98e944f8bffa99b7
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

Loading…