Nitrogen → HCID 90004229, 화합물

HRID 1771390노트

반응식

HRID 1771390 반응식
I[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[O:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[CH:17]([C:20]1[CH:24]=[C:23]([NH2:25])[NH:22][N:21]=1)([CH3:19])[CH3:18].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].N#N>C1(C)C=CC=CC=1.[Cu]I>[CH:17]([C:20]1[CH:24]=[C:23]([NH2:25])[N:22]([C:2]2[CH:16]=[CH:15][CH:14]=[C:4]([O:5][CH2:6][CH2:7][N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[CH:3]=2)[N:21]=1)([CH3:19])[CH3:18]

참가 물질

8

반응물 5

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 184035554-[2-(3-Iodophenoxy)ethyl]morpholineHCID 178439404HCID 178439404, 화합물

생성물 1

HCID 90004229HCID 90004229, 화합물

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매

실험 절차

To a solution of 4-(2-(3-iodophenoxyl)ethyl)morpholine (1.0 g, 2.9 mmol) in anhydrous toluene (20 mL) was added 3-isopropyl-1H-pyrazol-5-amine (397 mg, 3.17 mmol) followed by (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (227 μL, 1.44 mmol) and potassium carbonate (1.99 g, 14.4 mmol). The mixture was purged with N2, copper(I) iodide (82 mg, 0.43 mmol) was added and the reaction mixture was heated at reflux under N2 for 64 hr. The resulting mixture was cooled to RT and was partitioned between EtOAc and water (100 mL). The organic layer was separated and washed with brine (2×100 mL) and was then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 40 g, 0-20% MeOH in DCM, gradient elution) to afford the title compound, Intermediate A13, as a brown oil (325 mg, 33%); Rt 1.66 min (Method 2, basic); m/z 329 (M+H)+ (ES+).

후처리

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux under N2 for 64 hr
  4. customwas partitioned between EtOAc and water (100 mL)
  5. customThe organic layer was separated
  6. washwashed with brine (2×100 mL)
  7. customwas then dried
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography (SiO2, 40 g, 0-20% MeOH in DCM, gradient elution)

출처 및 근거

ORD 기록
ord-be5c611864ad4ccc91bacf8fab260a8f
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249125B2

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