Benzyl(2-methoxyethyl)amine → N-benzyl-N-ethyl-2-(4-methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamide

HRID 874209Notes

Reaction equation

HRID 874209 reaction equation
[CH3:1][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.[CH2:22]([NH:29][CH2:30][CH2:31]OC)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:22]([N:29]([CH2:30][CH3:31])[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]([CH3:1])=[CH:7][CH:6]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

3

Reactant 2

HCID 2396989Benzyl(2-methoxyethyl)amineHCID 185457122-(4-Methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid

Product 1

HCID 56591624N-benzyl-N-ethyl-2-(4-methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-acetamideYield 54.6%

Procedure

According to the method of Example 13, 2-(4-methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-acetic acid and N-benzyl-2-methoxyethylamine were used as raw materials for synthesis, to obtain yellow solid powder, yield 54.6%. m.p. 220-222° C., ESm/z: 398[M+H]+, 1H NMR(CDCl3, 400 MHz)δ: 1.14(t, 1.5H, J=7.00 Hz), 1.17(t, 1.5H, J=7.00 Hz), 2.36(s, 1.5H), 2.37(s, 1.5H), 2.52(s, 1.5H), 2.54(s, 1.5H), 3.35(q, 1H, J=7.00 Hz), 3.52(q, 1H, J=7.00 Hz), 4.15(s, 1H), 4.24(s, 1H), 4.57(s, 1H), 4.61(s, 1H), 7.05-7.19(m, 1H), 7.22-7.36(m, 9H), 7.47-7.62(m, 1H), 8.13-8.29(m, 1H).

Workup

  1. customwere used as raw materials for synthesis
  2. customto obtain yellow solid powder, yield 54.6%

Sources & evidence

ORD record
ord-8d336e0322ed4cdc95dabe3671a8b19d
Source dataset
uspto-grants-2015_03
Patent number
US08980887B2

Reaction notes

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