Diisopropylethylamine → (S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

HRID 2422529ノート

反応式

HRID 2422529 の反応式
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][C:11]([C:15]#[N:16])=[N:12]2)=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[N+:23]([C:26]1[CH:43]=[CH:42][C:29]([C:30]([O:32][C:33]([CH2:40][CH3:41])([C:36]([F:39])([F:38])[F:37])[C:34]#[CH:35])=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24].C(N(C(C)C)CC)(C)C>C1COCC1.[Cu](I)I>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([O:32][C@@:33]([C:34]2[N:3]=[N:2][N:1]([CH2:4][C:5]3[CH:14]=[C:13]4[C:8]([C:9]([C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:10][C:11]([C:15]#[N:16])=[N:12]4)=[CH:7][CH:6]=3)[CH:35]=2)([C:36]([F:37])([F:38])[F:39])[CH2:40][CH3:41])=[O:31])=[CH:42][CH:43]=1)([O-:25])=[O:24]

参加物

6

反応物 3

HCID 81531DiisopropylethylamineHCID 59774860HCID 59774860、化合物HCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoate

生成物 1

HCID 66791323(S)-1-{1-[(2-cyano-4-phenylquinolin-7-yl)methyl]-1H-1,2,3-triazol-4-yl}-1-(trifluoromethyl)propyl 4-nitrobenzoate

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-(azidomethyl)-4-phenylquinoline-2-carbonitrile (120 mg, 0.42 mmol) and 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (139 mg, 0.46 mmol, slower eluting enantiomer described in Example 1, step 2) in THF (5 mL) was added diisopropylethylamine (0.37 mL, 2.1 mmol) followed by copper iodide (120 mg, 0.63 mmol). The reaction was stirred at room temperature overnight and quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification on silica gel (eluting with EtOAc/hexanes, 4:6) gave the title compound. MS (+ESI): 587 (M+H)+.

後処理

  1. customquenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel (eluting with EtOAc/hexanes, 4:6)

出典と根拠

ORDレコード
ord-69d7c1497e7c4c2bbbb19dad87716a83
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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