Diisopropylethylamine → N-((4-chlorophenyl)(hydroxyimino)methyl)-4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanamide

HRID 1051402

反応式

HRID 1051402 の反応式
[F:1][C:2]([F:26])([F:25])[CH:3]([CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10]1)[CH2:4][C:5](O)=[O:6].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.[Cl:60][C:61]1[CH:70]=[CH:69][C:64]([C:65](=[N:67][OH:68])[NH2:66])=[CH:63][CH:62]=1.[Na+].[Cl-].O>CN(C=O)C>[Cl:60][C:61]1[CH:62]=[CH:63][C:64]([C:65](=[N:67][OH:68])[NH:66][C:5](=[O:6])[CH2:4][CH:3]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=3)[CH2:10]2)[C:2]([F:26])([F:1])[F:25])=[CH:69][CH:70]=1

参加物

7

反応物 5

HCID 81531DiisopropylethylamineHCID 2246504-chloro-N'-hydroxybenzenecarboximidamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57417360Sodium chloride; waterHCID 901035704,4,4-Trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid

生成物 1

HCID 137210851N-((4-chlorophenyl)(hydroxyimino)methyl)-4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In a 10 mL round-bottomed flask, 4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanoic acid (27 mg, 70.4 μmol) and HATU (26.8 mg, 70.4 μmol) were combined with DMF (1 ml) to give a colorless solution. DIEA (27.3 mg, 36.9 μl, 211 μmol) was added and the resulting mixture was stirred at room temperature for 10 min. 4-Chloro-N′-hydroxybenzimidamide (12.0 mg, 70.4 μmol) was added and the resulting mixture was stirred at room temperature for 4 hr. The reaction mixture was poured into 50 mL saturated NaCl/H2O (1:1) and extracted with ethyl acetate (2×25 mL). The organic layers were combined, washed with saturated NaCl (1×20 mL), H2O (2×50 mL), dried over MgSO4, filtered and concentrated in vacuo to give N-((4-chlorophenyl)-(hydroxyimino)methyl)-4,4,4-trifluoro-3-((3-(3-(trifluoromethyl)phenyl)piperidin-1-yl)methyl)butanamide as an oil, which was used as is for the next reaction.

後処理

  1. customto give a colorless solution
  2. stirringthe resulting mixture was stirred at room temperature for 4 hr
  3. extractionextracted with ethyl acetate (2×25 mL)
  4. washwashed with saturated NaCl (1×20 mL), H2O (2×50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7fbb614f5d2e424c95f4f22da6e8aeef
出典データセット
uspto-grants-2016_07
特許番号
US09388172B2

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