(E)-4-methylhex-2-enoic Acid → (E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

HRID 333985ノート

反応式

HRID 333985 の反応式
[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([OH:7])=O.[N:10]1([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>CN(C=O)C.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>[CH3:1][CH:2]([CH2:8][CH3:9])/[CH:3]=[CH:4]/[C:5]([N:13]1[CH2:14][CH2:15][N:10]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([C:26]([F:29])([F:27])[F:28])=[CH:23][CH:24]=3)[N:19]=[CH:18][CH:17]=2)[CH2:11][CH2:12]1)=[O:7]

参加物

6

反応物 2

HCID 5463168(E)-4-methylhex-2-enoic AcidHCID 114602054-Piperazin-1-yl-7-(trifluoromethyl)quinoline

生成物 1

HCID 86691602(E)-4-Methyl-1-[4-[7-(trifluoromethyl)-4-quinolyl]piperazin-1-yl]hex-2-en-1-one

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒2 回HCID 81531Diisopropylethylamine溶媒2 回HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)溶媒

実験手順

(E)-4-Methylhex-2-enoic acid (26 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), HATU was added (76 mg, 0.2 mmol) and the mixture was stirred at room temperature for 15 minutes. 4-piperazin-1-yl-7-(trifluoromethyl)quinoline (56 mg, 0.2 mmol) was dissolved in DMF (0.5 ml) together with diisopropylethylamine (35 μl), the two solutions were combined and stirred at room temperature overnight. The mixture was evaporated to dryness under reduced pressure and the residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 62.6 mg (0.16 mmol, 80%). MS (APCI) m/z=391.9 [M+1]+.

後処理

  1. additionwas added (76 mg, 0.2 mmol)
  2. stirringstirred at room temperature overnight
  3. customThe mixture was evaporated to dryness under reduced pressure
  4. customthe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  5. customto yield 62.6 mg (0.16 mmol, 80%)

出典と根拠

ORDレコード
ord-ffcff14e00e84e19a9757aa08db5402d
出典データセット
uspto-grants-2014_11
特許番号
US08883791B2

反応ノート

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