Diisopropylamine → HCID 68872500, 화합물

HRID 490204노트

반응식

HRID 490204 반응식
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[O:4].C(NC(C)C)(C)C.[N:23]1([C:29]2[N:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31]#[N:32])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1>C1(C)C=CC=CC=1>[C:31]([C:30]1[C:29]([N:23]2[CH2:24][CH2:25][N:26]([CH2:2][C:3]([NH:5][C:6]3[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=3)=[O:4])[CH2:27][CH2:28]2)=[N:36][CH:35]=[CH:34][CH:33]=1)#[N:32]

참가 물질

5

반응물 3

HCID 7912DiisopropylamineHCID 27364642-chloro-N-[4-(trifluoromethyl)phenyl]acetamideHCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrile

생성물 1

HCID 68872500HCID 68872500, 화합물수율 78.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

2-Chloro-N-(4-trifluoromethylphenyl)acetamide (820 mg, 3.45 mmol, Maybridge) and N,N-diisopropylamine (2.5 mL) in toluene (50 mL) were treated with 2-piperazin-1-ylnicotinonitrile (800 mg, 4.25 mmol, Chess) and heated to 60° C. for 18 hours. The mixture was allowed to cool to room temperature, transferred to a separatory funnel and washed with saturated aqueous sodium bicarbonate. The organic phase was dried (sodium sulfate), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (gradient elution with 20% to 40% ethyl acetate:hexanes) to provide 1.05 g (78% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.69 (m, 4H), 3.26 (s, 2H), 3.68 (m, 4H), 6.93 (dd, 1H, J=7.5, 4.7 Hz), 7.68 (AA′BB′, 2H, J=8.8 Hz), 7.88 (AA′BB′, 2H, J=8.5 Hz), 8.07 (dd, 1H, J=7.8, 2.0 Hz), 8.42 (dd, 1H, J=4.7, 2.0 Hz), 10.14 (br s, 1H); MS (DCI/NH3) m/e 390 (M+H)+;

후처리

  1. temperatureto cool to room temperature
  2. customtransferred to a separatory funnel
  3. washwashed with saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel (gradient elution with 20% to 40% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-7fc287a885eb4d4bab666d848b7c715b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528134B2

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