Cyclopropanecarboxylic acid → Cyclopropanecarboxylic acid [2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-amide

HRID 731645노트

반응식

HRID 731645 반응식
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([NH2:21])[CH:18]=[CH:17][N:16]2[CH:22]=1.[CH:23]1([C:26](O)=[O:27])[CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C.[Cl-].[Na+].O.O>CN(C=O)C>[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:3]=1[C:13]1[N:14]=[C:15]2[CH:20]=[C:19]([NH:21][C:26]([CH:23]3[CH2:25][CH2:24]3)=[O:27])[CH:18]=[CH:17][N:16]2[CH:22]=1

참가 물질

6

반응물 4

HCID 15655Cyclopropanecarboxylic acidHCID 81531DiisopropylethylamineHCID 23713072Sodium chloride dihydrateHCID 247388302-(5-Methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine

생성물 1

HCID 24738831Cyclopropanecarboxylic acid [2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-yl]-amide수율 12%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

A solution of 2-(5-methyl-3-phenyl-isoxazol-4-yl)-imidazo[1,2-a]pyridin-7-ylamine (92 mg, 0.32 mmol) in DMF (0.2 mL) was added to a solution containing cyclopropanecarboxylic acid (24.8 mg, 0.29 mmol), N,N,N′,N′-tetramethyl-O-(benzotriazol-1-yl)uranium tetrafluoroborate (101.7 mg, 0.32 mmol), N,N-diisopropyl ethyl amine (247 μL, 1.44 mmol) in DMF (0.3 mL) and the resulting mixture stirred at room temperature overnight and then heated at 110° C. for 2.5 h. The resulting mixture was then poured into a mixture of brine: water (1:1) and extracted with ethyl acetate. The combined organic layers were then washed with brine, dried over sodium sulphate and evaporated to leave a brown solid. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100) afforded the title compound (12.4 mg, 12%) which was obtained as an off-white solid. MS: m/e 359.0 [M+H]+.

후처리

  1. temperatureheated at 110° C. for 2.5 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were then washed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customto leave a brown solid
  7. customPurification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 0:100)

출처 및 근거

ORD 기록
ord-71e6d567bfd9432c81432372000248ed
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585874B2

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