Isopropylamine → 6-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-N-isopropyl-nicotinamide

HRID 1807494ノート

反応式

HRID 1807494 の反応式
C[Al](C)C.[CH:5]([NH2:8])([CH3:7])[CH3:6].CO[C:11](=[O:30])[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]2[C:21]([CH2:26][CH2:27][CH2:28][CH3:29])=[N:22][O:23][C:24]=2[CH3:25])=[N:14][CH:13]=1>C1(C)C=CC=CC=1.O1CCOCC1>[CH:5]([O:23][CH:24]([CH3:25])[CH3:20])([CH3:7])[CH3:6].[CH2:26]([C:21]1[C:20]([CH2:19][O:18][C:15]2[CH:16]=[CH:17][C:12]([C:11]([NH:8][CH:5]([CH3:7])[CH3:6])=[O:30])=[CH:13][N:14]=2)=[C:24]([CH3:25])[O:23][N:22]=1)[CH2:27][CH2:28][CH3:29]

参加物

7

反応物 3

HCID 6363IsopropylamineHCID 16682925TrimethylaluminumHCID 665991586-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester

生成物 2

HCID 7914Diisopropyl EtherHCID 498047566-(3-Butyl-5-methyl-isoxazol-4-ylmethoxy)-N-isopropyl-nicotinamide収率 30.6%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
90 °C

実験手順

Trimethylaluminium (3 mL of a 2 M solution in toluene, 6 mmol) was added dropwise to a stirred solution of isopropylamine (355 mg, 6.0 mmol) in dioxane (4 mL) at room temperature and under argon. After 1 h, a solution of 6-(3-butyl-5-methyl-isoxazol-4-ylmethoxy)-nicotinic acid methyl ester (537 mg, 1.5 mmol) in dioxane (4 mL) was added and the reaction mixture warmed to 90° C. After 2 h the reaction mixture was cooled and poured onto ice/water. The resultant mixture was extracted with ethyl acetate then the combined extracts were washed with Seignette salt solution. The organic phase was dried, filtered and evaporated then purified by chromatography (silica, 0 to 60% ethyl acetate in heptane) then trituration with diisopropyl ether to give the title compound (76 mg, 15%) as a white solid. MS: m/e=332.4 [M+H]+.

後処理

  1. temperatureAfter 2 h the reaction mixture was cooled
  2. additionpoured onto ice/water
  3. extractionThe resultant mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with Seignette salt solution
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated
  8. customthen purified by chromatography (silica, 0 to 60% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-32b91403c47441a58bc7cde75647b43a
出典データセット
uspto-grants-2013_01
特許番号
US08357703B2

反応ノート

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