Diisopropylethylamine → 1-({2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetyl)piperidin-4-one

HRID 1750345ノート

反応式

HRID 1750345 の反応式
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23](O)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O.Cl.[NH:61]1[CH2:66][CH2:65][C:64](=[O:67])[CH2:63][CH2:62]1>CN(C=O)C.O>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([F:16])=[CH:14][CH:15]=2)=[C:8]([C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([N:61]3[CH2:66][CH2:65][C:64](=[O:67])[CH2:63][CH2:62]3)=[O:24])[N:21]=2)[CH:7]=[N:6]1)([CH3:3])([CH3:2])[CH3:4]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 2723901PiperonylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867211822-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid

生成物 1

HCID 867211831-({2-[1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl]-1,3-thiazol-4-yl}acetyl)piperidin-4-one収率 60%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of the compound (60 mg, 0.17 mmol) obtained in step 6, HATU (76 mg, 0.20 mmol), DIEA (0.035 mL, 0.20 mmol) and piperidin-4-one monohydrochloride monohydrate (30.8 mg, 0.20 mmol) in DMF (1.5 mL) was stirred at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane) to give the title compound (44 mg, 0.100 mmol, 60%) as a white powder.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 5→100% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-2fdb94dfbcd84cf2a725b7855591916e
出典データセット
uspto-grants-2015_10
特許番号
US09156837B2

反応ノート

読み込み中…