Potassium Hydroxide → 3-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

HRID 414272

반응식

HRID 414272 반응식
[OH:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]3=[N:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:20]([N:24]([CH2:29][CH2:30][CH2:31]Cl)[CH2:25][CH2:26][CH2:27][CH3:28])[CH2:21][CH2:22][CH3:23].[OH-].[K+]>CO>[CH2:25]([N:24]([CH2:29][CH2:30][CH2:31][O:1][C:2]1[CH:19]=[CH:18][C:5]([C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[C:16]([CH3:17])[C:11]3=[N:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1)[CH2:20][CH2:21][CH2:22][CH3:23])[CH2:26][CH2:27][CH3:28]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 96084N-(3-Chloropropyl)dibutylamineHCID 142014553-(4-Hydroxybenzoyl)-8-methylimidazo[1,2-a]pyridine

생성물 1

HCID 102737383-(4-Dibutylaminopropoxybenzoyl)-8-methylimidazo[1,2-a]pyridine

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 3-(4-hydroxybenzoyl)-8-methylimidazo[1,2-a]pyridine (2.3 g, 9.6 mmol), dibutylaminopropyl chloride (6.8 g, 33 mmol) and potassium hydroxide (1.3 g, 23 mmol) in methanol (60 ml) was stirred at reflux for 96 hours. The mixture was concentrated and the resulting oil was flash chromatographed (silica gel, 2.5% methanol in diethyl ether) to give 1.3 g (31% yield) of the free base of the title compound. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the free base in methanol, concentrated and recrystallized from acetone-ether to give the HCl salt of the title compound as an off-white solid, mp 105° C. to 107° C. IR(KBr): 3440, 2640, 1645, 1605 cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ9.66 (d, J=8 Hz, 1H), 8.74 (s, 1H), 8.00-7.61 (m, 4H), 7.20 (d, J=7.2 Hz, 2H), 4.29 (t, J=5 Hz, 2H), 3.41-3.15 (m, 6H), 2.75 (s, 3H), 2.31 (m, 2H), 1.80-1.42 (m, 8H), 1.02 (m, 6H).

후처리

  1. temperatureat reflux for 96 hours
  2. concentrationThe mixture was concentrated
  3. customchromatographed (silica gel, 2.5% methanol in diethyl ether)

출처 및 근거

ORD 기록
ord-04cd127fc1034615817c748a7c7dcfef
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791117

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