Potassium Carbonate → HCID 117729754、化合物

HRID 60659

反応式

HRID 60659 の反応式
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:12]1[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>[Cu]I>[NH2:10][C:8]1[N:7]([C:12]2[CH:13]=[C:14]([OH:19])[CH:15]=[C:16]([Cl:18])[CH:17]=2)[N:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:9]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 226301803-Bromo-5-chlorophenolHCID 178441179HCID 178441179、化合物

生成物 1

HCID 117729754HCID 117729754、化合物収率 62%

試薬・触媒・溶媒 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒

反応条件

温度
110 °C

実験手順

A microwave vial containing 3-tert butyl-1h-pyrazol-5-amine (559 mg, 4.02 mmol), Intermediate 62a (1.00 g, 4.82 mmol), copper(I) iodide (38 mg, 0.20 mmol) and potassium carbonate (1.16 g, 8.44 mmol) was repeatedly purged with argon. Trans-N,N′-dimethylcyclohexane-1,2-diamine (126 μL, 0.80 mmol) was added and the mixture was re-purged with argon. Degassed toluene (4 mL) was added and the resulting suspension was stirred and heated at 110° C. for 24 h. The cooled suspension was passed through Celite pad and diluted with water and extracted with EtOAc. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-50% EtOAc in cyclohexane, to give the title compound (620 mg, 62%). LCMS (Method 3): Rt 3.13 min, m/z 266 [MH+].

後処理

  1. customwas repeatedly purged with argon
  2. customthe mixture was re-purged with argon
  3. additionDegassed toluene (4 mL) was added
  4. additiondiluted with water
  5. extractionextracted with EtOAc
  6. customThe combined organics were dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-c7423d7095ec4c6a83aa424725e57a0d
出典データセット
uspto-grants-2016_09
特許番号
US09440974B2

関連ノート

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