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

HRID 2422552노트

반응식

HRID 2422552 반응식
[N:1]([CH2:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)=[CH:10][C:11]([Cl:15])=[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:16]5[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=5)=[CH:10][C:11]([Cl:15])=[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]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 597748703-(Trifluoromethyl)pent-1-YN-3-YL 4-nitrobenzoateHCID 866219807-(Azidomethyl)-2-chloro-4-(4-fluorophenyl)quinoline

생성물 1

HCID 86621981(S)-1-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 7-(azidomethyl)-2-chloro-4-(4-fluorophenyl)quinoline (500 mg, 1.60 mmol), 1-ethyl-1-(trifluoromethyl)prop-2-yn-1-yl 4-nitrobenzoate (529 mg, 1.76 mmol), copper iodide (456 mg, 2.4 mmol) and diisopropylethylamine (1.4 mL, 8.04 mmol) in THF (10 mL) was stirred at rt for 16 h. The reaction was 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): 614 (M+H)+.

후처리

  1. customThe reaction was quenched 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)

출처 및 근거

ORD 기록
ord-987babdab24a43b3aa17ae2d94b48223
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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