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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
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HRID 1191211 반응식
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
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참가 물질

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반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-db5452fa3afc464e81a58718a80db788
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08680098B2

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