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Pyridine → (5-tert-Butyl-2-{3-[(2-dimethylamino-ethyl)-methyl-amino]-phenyl}-2H-pyrazol-3-yl)-carbamic acid phenyl ester

HRID 630960
ノート
印刷プレビュー

反応式

HRID 630960 の反応式
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([N:13]([CH3:19])[CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH:10]=[CH:11][CH:12]=2)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=1.N1C=CC=CC=1.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:32]>C(Cl)Cl.O>[C:34]1([O:33][C:31](=[O:32])[NH:1][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[C:9]([N:13]([CH2:14][CH2:15][N:16]([CH3:18])[CH3:17])[CH3:19])[CH:8]=3)[N:5]=[C:4]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:3]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1049Pyridine2 回HCID 15891Phenyl chloroformate2 回HCID 89612440HCID 89612440、化合物

生成物 1

HCID 86687275(5-tert-Butyl-2-{3-[(2-dimethylamino-ethyl)-methyl-amino]-phenyl}-2H-pyrazol-3-yl)-carbamic acid phenyl ester収率 43%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

A solution of Intermediate 150b (50 mg, 0.16 mmol) in DCM (2 mL) was treated with pyridine (26 μL, 0.32 mmol) and phenyl chloroformate (32 μL, 0.25 mmol). The resulting mixture was stirred at RT for 2 h. Further pyridine (26 μL, 0.32 mmol) and phenyl chloroformate (32 μL, 0.25 mmol) were added and the mixture stirred at RT for 16 h. The mixture was diluted with water and the phases separated. The aqueous layer was extracted with DCM and the combined organic phase was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was purified by FCC, using 0-20% MeOH in DCM, to give the title compound (30 mg, 43%). LCMS (Method 3): Rt 2.97 min, m/z 436 [MH+].

後処理

  1. stirringthe mixture stirred at RT for 16 h
  2. customthe phases separated
  3. extractionThe aqueous layer was extracted with DCM
  4. washthe combined organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by FCC

出典と根拠

ORDレコード
ord-a67d246ad31f4a3ea12c0a1b11e77a9d
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09315503B2

反応ノート

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