2-(4-Chloropropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine → 2-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

HRID 2350941

反応式

HRID 2350941 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]([C:10]([C:12]2[N:13]=[C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]3[CH:21]=2)=[O:11])=[CH:8][CH:7]=1>C(NCCCC)CCC>[CH2:12]([N:13]([CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:23]=[CH:22][C:9]([C:10]([C:12]2[N:13]=[C:14]3[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]3[CH:21]=2)=[O:11])=[CH:8][CH:7]=1)[CH2:14][CH2:19][CH2:18][CH3:17])[CH2:10][CH2:9][CH3:8]

参加物

3

反応物 1

HCID 142014812-(4-Chloropropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

生成物 1

HCID 102957542-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine収率 197.7%

試薬・触媒・溶媒 1

HCID 8148Dibutylamine溶媒

実験手順

A mixture of 2-(4-chloropropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine (2.4 g, 6.0 mmol) in dibutylamine (30 ml) was stirred at reflux for 8 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, acetone) to give the free base of the title compound (2.5 g, 100% yield) as a thick oil. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the title compound in methanol, concentrated and recrystallized from methanol-acetone, mp 159° C. to 161° C. IR(KBr): 3420, 1650 cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ 8.89 (s, 1H), 8.72 (d, J=6.6 Hz, 1H), 8.15 (d, J=8.9 Hz, 2H), 7.89 (d, J=7.3 Hz, 1H), 7.48 (t, J=6.9 Hz, 1H), 7.21 (d, J= 8.9 Hz, 2H), 4.29 (t, J=7 Hz, 2H), 3.26 (m, 6H), 2.73 (s, 3H), 2.33 (m, 2H), 1.79-1.35 (m, 8H), 1.02 (m, 6H).

後処理

  1. temperatureat reflux for 8 hours
  2. customThe excess dibutylamine was removed by distillation
  3. customchromatographed (silica gel, acetone)

出典と根拠

ORDレコード
ord-51ea386579a744b29511e8ea06e809fa
出典データセット
uspto-grants-1989_10
特許番号
US04871745

関連ノート

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