N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide → N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

HRID 1497916

反応式

HRID 1497916 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][C:15](=[O:17])[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[NH:18][C:19]([C:21]1[N:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]2=[N:23][CH:22]=1)=[O:20].[CH:30]1([Mg]Br)[CH2:32][CH2:31]1>C1COCC1>[CH:30]1([C:15]2([OH:17])[CH2:16][CH:13]([C:11]3[O:10][N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:18][C:19]([C:21]5[N:25]6[CH:26]=[CH:27][CH:28]=[CH:29][C:24]6=[N:23][CH:22]=5)=[O:20])[CH:4]=4)[N:12]=3)[CH2:14]2)[CH2:32][CH2:31]1

参加物

4

反応物 2

HCID 71280448N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamideHCID 178418630HCID 178418630、化合物

生成物 1

HCID 71280497N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirring solution of N-(2-methyl-5-(5-(3-oxocyclobutyl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (10) (250 mg, 0.645 mmol) in anhydrous THF (10 mL) at −78° C. under Argon was added cyclopropylmagnesium bromide (2.6 mL, 1.3 mmol). The reaction was stirred for 30 minutes at room temperature and quenched with 1N HCl at 0° C. The crude product was extracted with ethylacetate. The organic layer was washed with saturated ammonium chloride, water and dried over anhydrous sodium sulfate. The crude product was purified by silica chromatography to give N-(5-(5-(3-cyclopropyl-3-hydroxycyclobutyl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F31). 1H NMR (400 MHz, d6-DMSO) δ 10.04 (s, 1H), 9.47-9.45 (m, 1H), 8.59 (s, 1H), 8.07 (d, J=1.6 Hz, 1H), 7.83-7.76 (m, 2H), 7.55-7.52 (m, 1H), 7.49 (d, J=8.0 Hz, 1H), 7.20-7.16 (m, 1H), 5.19 (s, 1H), 4.37-4.35 (m, 1H), 3.46-3.40 (m, 1H), 2.45-2.40 (m, 2H), 2.36 (s, 3H), 1.54-1.41 (m, 2H), 1.19-1.14 (m, 1H), 0.34-0.26 (m, 2H), 0.22-0.11 (m, 1H). MS m/z 430.47 (M+1)+.

後処理

  1. customquenched with 1N HCl at 0° C
  2. extractionThe crude product was extracted with ethylacetate
  3. washThe organic layer was washed with saturated ammonium chloride, water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe crude product was purified by silica chromatography

出典と根拠

ORDレコード
ord-4db6ada5fc5146af883ee5f86192b59d
出典データセット
uspto-grants-2015_12
特許番号
US09199981B2

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