2-(Piperazin-1-yl)pyridine-3-carbonitrile → 2-(4-(7-(Cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile

HRID 2037039노트

반응식

HRID 2037039 반응식
Cl[C:2]1[C:7]([CH3:8])=[C:6]([N:9]([CH:17]2[CH2:19][CH2:18]2)C(=O)OC(C)(C)C)[N:5]2[N:20]=[CH:21][C:22]([CH:23]=[O:24])=[C:4]2[N:3]=1.[N:25]1([C:31]2[N:38]=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]#[N:34])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(O)(C)C>[CH:17]1([NH:9][C:6]2[N:5]3[N:20]=[CH:21][C:22]([CH:23]=[O:24])=[C:4]3[N:3]=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([C:31]4[N:38]=[CH:37][CH:36]=[CH:35][C:32]=4[C:33]#[N:34])[CH2:26][CH2:27]3)[C:7]=2[CH3:8])[CH2:18][CH2:19]1

참가 물질

4

반응물 2

HCID 27372032-(Piperazin-1-yl)pyridine-3-carbonitrileHCID 86652158Tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate

생성물 1

HCID 583141322-(4-(7-(Cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile수율 58.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

반응 조건

온도
90 °C

실험 절차

Tert-butyl 5-chloro-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-7-yl(cyclopropyl)carbamate (60 mg, 0.17 mmol) was mixed with 2-(piperazin-1-yl)nicotinonitrile (64 mg, 0.34 mmol) in i-propanol (1 mL). The reaction mixture was heated at 90° C. in the microwave for 1 hour. The reaction was cooled to room temperature and concentrated under vacuum. The residue was dissolved in (1:1) TFA/DCM (4 mL) and stirred at room temperature for 1 hour. The reaction was evaporated to dryness, quenched with 3N NaOH, filtered, washed with water, and dried under vacuum The product, 2-(4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile, was further purified by preparative TLC using 5% acetone/dichloromethane as the eluent (40 mg, 58% yield). LCMS (M+1=403)

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was dissolved in (1:1) TFA/DCM (4 mL)
  4. customThe reaction was evaporated to dryness
  5. customquenched with 3N NaOH
  6. filtrationfiltered
  7. washwashed with water
  8. dry with materialdried under vacuum The product, 2-(4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-yl)piperazin-1-yl)nicotinonitrile
  9. customwas further purified by preparative TLC

출처 및 근거

ORD 기록
ord-60f92a34267949e98b2fe6324558526b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575177B2

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