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Potassium Carbonate → 3-tert-Butyl-1'-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1'H-[1,4']bipyrazolyl-5-ylamine

HRID 630898
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HRID 630898 반응식
I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:6]=1.[C:17]([C:21]1[CH:22]=[C:23]([NH2:26])[NH:24][N:25]=1)([CH3:20])([CH3:19])[CH3:18].C([O-])([O-])=O.[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I.O.C1(C)C=CC=CC=1>[C:17]([C:21]1[CH:22]=[C:23]([NH2:26])[N:24]([C:2]2[CH:3]=[N:4][N:5]([CH2:7][CH2:8][CH2:9][O:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH:6]=2)[N:25]=1)([CH3:20])([CH3:19])[CH3:18]
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 866871804-Iodo-1-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1H-pyrazoleHCID 178441179HCID 178441179, 화합물

생성물 1

HCID 866871823-tert-Butyl-1'-[3-(tetrahydro-pyran-2-yloxy)-propyl]-1'H-[1,4']bipyrazolyl-5-ylamine수율 73.6%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매
HCID 962Water용매
HCID 1140Toluene용매

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온도
140 °C

실험 절차

To a mixture of intermediate 113a (1.50 g, 4.46 mmol), 5-tert-butyl-2H-pyrazol-3-ylamine (620 mg, 4.46 mmol), copper (I) iodide (42 mg, 0.22 mmol) and K2CO3 (1.29 g, 9.37 mmol) was added a solution of toluene (4.6 mL), previously degassed by using a stream of argon. (R,R)-(−)-N,N′-Dimethyl-1,2-cyclohexanediamine (141 μL, 0.89 mmol) was then added and the reaction mixture was heated at 140° C. for 2.5 h under microwave irradiation. The crude reaction mixture was poured into water and extracted with EtOAc (×3). The combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by FCC on silica, using a gradient of 0-100% EtOAc in cyclohexane, to give the title compound (1.14 g, 73%). LCMS (Method 4): Rt 2.34 min, m/z 348 [MH+].

후처리

  1. custompreviously degassed
  2. customThe crude reaction mixture
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by FCC on silica

출처 및 근거

ORD 기록
ord-89ab88770c214d0f8c355d3ba8b6058f
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09315503B2

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