Diisopropylethylamine → 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-isonicotinamide

HRID 1611940ノート

反応式

HRID 1611940 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][O:45][C:46]1[C:51]2[N:52]=[C:53]([NH2:55])[O:54][C:50]=2[C:49]([CH:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)=[CH:48][CH:47]=1>C1COCC1.O1CCOCC1.CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([NH:55][C:53]1[O:54][C:50]2[C:49]([CH:56]3[CH2:57][CH2:58][O:59][CH2:60][CH2:61]3)=[CH:48][CH:47]=[C:46]([O:45][CH3:44])[C:51]=2[N:52]=1)=[O:7]

参加物

9

反応物 4

HCID 81531DiisopropylethylamineHCID 2227012-Bromoisonicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 222522334-Methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine

生成物 1

HCID 222522322-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-isonicotinamide収率 84.4%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirred solution of 106 mg (0.52 mmol) 2-bromo-isonicotinic acid in 5 ml THF were added 230 mg (0.60 mmol) HATU and 0.10 ml (0.60 mmol) N-ethyldiisopropyl-amine and stirring continued at room temperature for 5 h. A solution of 100 mg (0.40 mmol) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-ylamine in 5 ml dioxane and 1 ml DMF was then added and stirring continued at 40° C. for 72 h. The reaction mixture was then poured into 100 ml water and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (dichoromethane then methanol/dichloromethane 20/80) followed by trituration in ether afforded 146 mg (84%) 2-bromo-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzooxazol-2-yl]-isonicotinamide as a white crystalline solid. ES-MS m/e (%): 434 (M{81Br}+H+, 95), 432 (M{79Br}+H+, 100).

後処理

  1. stirringstirring
  2. waitcontinued at 40° C. for 72 h
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f70d28d890fd4d42b970ff234391dcca
出典データセット
uspto-grants-2006_01
特許番号
US06992083B2

反応ノート

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