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tert-Butanol → Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate

HRID 2391189
ノート
印刷プレビュー

反応式

HRID 2391189 の反応式
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20](C(O)=O)[N:21]=2)[N:18]=1)=[O:7].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.C([N:52]([CH2:55]C)CC)C.[C:57]([OH:61])([CH3:60])([CH3:59])[CH3:58]>C(OCC)(=O)C>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][CH:30]=1)[C:6]([NH:8][C:9]1[CH:10]=[C:11]([CH:25]=[CH:26][CH:27]=1)[O:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([CH:19]=[C:20]([NH:52][C:55](=[O:40])[O:61][C:57]([CH3:60])([CH3:59])[CH3:58])[N:21]=2)[N:18]=1)=[O:7]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 573875936-(3-{[3-(Trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid

生成物 1

HCID 57387816Tert-butyl [6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazin-2-yl]carbamate収率 39%

試薬・触媒・溶媒

1
HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 6-(3-{[3-(trifluoromethyl)benzoyl]amino}phenoxy)imidazo[1,2-b]pyridazine-2-carboxylic acid (111 mg, 0.25 mmol), diphenylphosphoryl azide (103 mg, 0.375 mmol), triethylamine (51 mg, 0.5 mmol) and tert-butanol (5.0 mL) was stirred at room temperature for 5 min, heated to 100° C. and stirred overnight. After allowing the reaction mixture to cool to room temperature, ethyl acetate was added to the mixture, and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19→ethyl acetate alone) to give the title compound (79 mg, 39%) as a white solid.

後処理

  1. temperatureheated to 100° C.
  2. stirringstirred overnight
  3. temperatureto cool to room temperature
  4. washthe mixture was washed with saturated aqueous sodium hydrogencarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/19→ethyl acetate alone)

出典と根拠

ORDレコード
ord-24fb434191e44aa7b02b517b37e6f555
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08273741B2

反応ノート

読み込み中…

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