Triethylamine → HCID 178514512, 화합물

HRID 626699노트

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HRID 626699 반응식
[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[CH:10]=O)=[N+:2]=[N-:3].[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([Cl:20])[C:14]=1[NH2:21].C(N(CC)CC)C>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[N:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1/[CH:10]=[N:21]/[C:14]1[C:13]([Cl:12])=[CH:18][C:17]([F:19])=[CH:16][C:15]=1[Cl:20])=[N+:2]=[N-:3]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27740082,6-Dichloro-4-fluoroanilineHCID 866970374-Azidopyridine-3-carbaldehyde

생성물 1

HCID 178514512HCID 178514512, 화합물수율 99.8%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Titanium tetrachloride (1M, 4.0 mL, 4.15 mmol) was added to a cooled (0° C.) mixture of 4-azidopyridine-3-carbaldehyde (1.0 g, 6.75 mmol), 2,6-dichloro-4-fluorophenylamine (1.22 g, 6.75 mmol) and triethylamine (2.8 mL, 20.3 mmol) in DCM (24 mL), under nitrogen. The reaction was stirred for 30 minutes at 0° C., warmed to room temperature, stirred for an additional 2 h, and concentrated under reduced pressure. The residue was dissolved in toluene and filtered though a pad of Celite®. The filtrate was concentrated to dryness under reduced pressure to afford the title compound as a yellow solid (2.09 g, quant.). This crude material was employed in the next step without further purification or analysis.

후처리

  1. temperaturea cooled
  2. temperaturewarmed to room temperature
  3. stirringstirred for an additional 2 h
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in toluene
  6. filtrationfiltered though a pad of Celite®
  7. concentrationThe filtrate was concentrated to dryness under reduced pressure

출처 및 근거

ORD 기록
ord-95e5fc1900274ec280eaa8e0f08f5c1a
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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