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1,2-Dimethoxyethane → 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-amide

HRID 1191211
ノート
印刷プレビュー

反応式

HRID 1191211 の反応式
Br[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.COCCOC.[C:16]([C:20]1[C:21]([Cl:29])=[C:22]([C:26](Cl)=[O:27])[N:23]([CH3:25])[N:24]=1)([CH3:19])([CH3:18])[CH3:17].[NH4+].[Cl-].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CCOC(C)=O.O>[Br:8][C:6]1[N:7]=[C:2]([NH:39][CH2:38][C:37]2[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[C:3]([NH:9][C:26]([C:22]2[N:23]([CH3:25])[N:24]=[C:20]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:21]=2[Cl:29])=[O:27])=[N:4][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 80711,2-DimethoxyethaneHCID 25517Ammonium ChlorideHCID 754524-MethoxybenzylamineHCID 6200042-Amino-3,5-dibromopyrazineHCID 866574055-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carbonyl chloride

生成物 1

HCID 866574125-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-amide

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of 3,5-dibromo-pyrazin-2-ylamine (252 mg, 1.00 mmol) in DME (10 mL) 60% NaH (120 mg, 3.00 mmol) was added portion wise. The resulting mixture was stirred at room temperature for 30 min and then treated with 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carbonyl chloride (234 mg, 1.00 mmol, prepared as described in Example 1, STEP C). The resulting mixture was stirred at room temperature for 2 h and treated with saturated NH4Cl (20 mL) followed by EtOAc (20 mL). The organic layer was separated, dried (Na2SO4) and concentrated. The resulting residue was dissolved in 1,4-dioxane (10 mL) and treated with 4-methoxybenzylamine (0.650 mL, 5.00 mmol). The resulting mixture was stirred at 65° C. for 2 h. The resulting mixture was allowed to cool to room temperature and then treated with water (10 mL) and EtOAc (20 mL). The organic layer was separated, dried (Na2SO4) and concentrated. The resulting residue was purified on silica (0:100-50:50 EtOAc:hexane) to yield 5-tert-butyl-4-chloro-2-methyl-2H-pyrazole-3-carboxylic acid [5-bromo-3-(4-methoxy-benzylamino)-pyrazin-2-yl]-amide. 1H-NMR (400 MHz, CDCl3) δ: 8.77 (br. s., 1H), 7.70 (s, 1H), 7.34 (d, J=8.6 Hz, 2H), 6.88 (d, J=8.6 Hz, 2H), 6.28-6.36 (m, 1H), 4.59 (d, J=5.1 Hz, 2H), 4.08 (s, 3H), 3.80 (s, 3H), 1.40 (s, 9H).

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 2 h
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. dissolutionThe resulting residue was dissolved in 1,4-dioxane (10 mL)
  6. stirringThe resulting mixture was stirred at 65° C. for 2 h
  7. temperatureto cool to room temperature
  8. customThe organic layer was separated
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customThe resulting residue was purified on silica (0:100-50:50 EtOAc:hexane)

出典と根拠

ORDレコード
ord-db5452fa3afc464e81a58718a80db788
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680098B2

反応ノート

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