Dimethyl Sulfoxide → N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide

HRID 230804노트

반응식

HRID 230804 반응식
C(N(CC)CC)C.CS(C)=O.[OH:12][CH2:13][CH2:14][CH2:15][C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:28][CH:27]=3)=[CH:20][N:19]2[C:41]=1[CH3:42]>O>[CH3:42][C:41]1[N:19]2[CH:20]=[C:21]([NH:24][C:25](=[O:40])[C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=4)=[CH:30][CH:31]=3)[CH:22]=[CH:23][C:18]2=[N:17][C:16]=1[CH2:15][CH2:14][CH:13]=[O:12]

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 57763130N-[2-(3-hydroxypropyl)-3-methylimidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide

생성물 1

HCID 86615940N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide수율 54.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Triethylamine (87.9 μL) and sulfur trioxide-pyridine complex (46.3 mg) were added to a DMSO solution (3 mL) of the compound (20.0 mg) obtained in Example 14, at room temperature. After stirred for 11 hours, the reaction liquid was poured into saturated saline water, and extracted with chloroform. The organic layer was dried with sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8) to obtain N-[3-methyl-2-(3-oxopropyl)imidazo[1,2-a]pyridin-6-yl]-4-(pyridin-2-ylmethoxy)benzamide (10.8 mg).

후처리

  1. customthe reaction liquid
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified through silica gel chromatography (methanol/chloroform=1/25 to 1/8)

출처 및 근거

ORD 기록
ord-735b33487d054610a492fbf6682aca76
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07566781B2

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