Ethyl Acetate → 2-[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-ethynylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

HRID 1770384

反応式

HRID 1770384 の反応式
C(N[C:5]1[CH:10]=[CH:9][C:8](S(N=[N+]=[N-])(=O)=O)=[CH:7][CH:6]=1)(=O)C.O=[C:18](C)[CH2:19]P(=O)(OC)OC.[F:27][CH:28]([F:64])[C:29]1[CH:33]=[C:32]([CH:34]([F:36])[F:35])[N:31]([CH2:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51]4[CH2:55][CH:54](C5C=CC=CC=5C=O)[O:53][N:52]=4)[N:50]=3)[CH2:42][CH2:41]2)=[O:39])[N:30]=1.C(OCC)(=O)C>C(#N)C.CO.O>[F:64][CH:28]([F:27])[C:29]1[CH:33]=[C:32]([CH:34]([F:36])[F:35])[N:31]([CH2:37][C:38]([N:40]2[CH2:45][CH2:44][CH:43]([C:46]3[S:47][CH:48]=[C:49]([C:51]4[CH2:55][CH:54]([C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=5[C:18]#[CH:19])[O:53][N:52]=4)[N:50]=3)[CH2:42][CH2:41]2)=[O:39])[N:30]=1

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 51291854-Acetamidobenzenesulfonyl azideHCID 866575662-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-benzaldehyde

生成物 1

HCID 866575652-[3,5-Bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-ethynylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 4-acetamidobenzenesulphonyl azide (140 mg) in acetonitrile (10 ml) was added, at room temperature, dimethyl 2-oxopropylphosphonate (97 mg). After stirring for 2 hours, 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}benzaldehyde (267 mg) in methanol (2 ml) was added to the reaction mixture. After stirring for 8 hours, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[5-(2-ethynylphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone (50 mg).

後処理

  1. stirringAfter stirring for 8 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic extracts were dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-dd4a76f51c5c49f09becc78f1c1f6e49
出典データセット
uspto-grants-2016_02
特許番号
US09247748B2

関連ノート

読み込み中…