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Ethylenediamine → 4-[4-(3,5-difluorobenzoyl)piperazin-1-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile

HRID 1772768
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HRID 1772768 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](Cl)=[O:6].Cl.[N:13]1([CH2:19][CH:20]([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][N:35](COCC[Si](C)(C)C)[C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:21][C:22]#[N:23])[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(CC)CC)C.FC(F)(F)C(O)=O.C(N)CN>C(#N)C.CO.C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([N:16]1[CH2:15][CH2:14][N:13]([CH2:19][CH:20]([N:24]2[CH:28]=[C:27]([C:29]3[C:30]4[CH:37]=[CH:36][NH:35][C:31]=4[N:32]=[CH:33][N:34]=3)[CH:26]=[N:25]2)[CH2:21][C:22]#[N:23])[CH2:18][CH2:17]1)=[O:6]
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참가 물질

9

반응물 5

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 1456003,5-Difluorobenzoyl chlorideHCID 670549114-piperazin-1-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride

생성물 1

HCID 50995642
4-[4-(3,5-difluorobenzoyl)piperazin-1-yl]-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile

시약·촉매·용매 3

HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매

실험 절차

3,5-Difluorobenzoyl chloride (8.44 mg, 0.0478 mmol), 4-piperazin-1-yl-3-[4-(7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]butanenitrile hydrochloride (from example 1, step 4; 0.02 g, 0.0398 mmol) and triethylamine (16.6 μL, 0.119 mmol) were mixed in acetonitrile (0.2 mL). The mixture was stirred at RT for 1 h. Solvents were evaporated. The crude product was treated with DCM (0.2 mL) and trifluoroacetic acid (0.2 mL, 0.002 mol) for 30 min. The reaction mixture was evaporated under reduced pressure. To the resultant residue was added methanol (1 mL) and ethylenediamine (0.1 mL, 0.001 mol). The reaction mixture was stirred at RT for 30 min and concentrated under reduced pressure. The residue was purified on RP-HPLC (XBridge C-18 Column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH, at flow rate 30 mL/min) to give the desired product. LCMS calculated for C24H23F2N8O(M+H)+: m/z=477.2; Found: 477.0.

후처리

  1. customSolvents were evaporated
  2. customThe reaction mixture was evaporated under reduced pressure
  3. stirringThe reaction mixture was stirred at RT for 30 min
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified on RP-HPLC (XBridge C-18 Column
  6. washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH, at flow rate 30 mL/min)

출처 및 근거

ORD 기록
ord-9cbe6f915fe344268a22f46498ab23e9
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249145B2

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