Dichloromethane → HCID 10019969, 화합물

HRID 2375376노트

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HRID 2375376 반응식
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:5]=1[CH3:20])(=O)[CH3:2].[CH2:21]1[CH:23]([C:24](Cl)=O)C1.[Sn](Cl)(Cl)(Cl)Cl.[CH2:32](Cl)Cl.[NH2:35][NH2:36]>C1(C)C=CC=CC=1.[OH-].[Na+].C(O)C.O>[CH:23]1([C:32]2[C:8]3=[C:7]([CH3:9])[N:6]([C:10]4[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=4[O:18][CH3:19])[C:5]([CH3:20])=[C:4]3[C:1]([CH3:2])=[N:36][N:35]=2)[CH2:24][CH2:21]1

참가 물질

10

반응물 5

HCID 6344DichloromethaneHCID 9321HydrazineHCID 24287Tin tetrachlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 393723951-[1-(2,4-Dimethoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl]ethan-1-one

생성물 1

HCID 10019969HCID 10019969, 화합물

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 3-acetyl-1-(2,4-dimethoxyphenyl)-2,5-dimethylpyrrole (273 mg, 1.0 mmol) in toluene (5 mL) at −78° C. was added 3-cyclopropanecarbonyl chloride (0.11 mL, 1.2 mmol) followed by dropwise addition of a 1.0M solution of tin(IV) chloride in CH2Cl2 (1.2 mL, 1.2 mmol). The reaction was allowed to warm to room temp overnight. The solution was diluted with 0.25M NaOH, extracted with EtOAc, the organic layer washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography (10-25% EtOAc/hexanes) to give the dione (MS (ESI) 342 (M +H)+). The dione was taken up in ethanol (5 mL) and excess hydrazine (0.1 mL) was added. The solution was stirred at 40° C. overnight, poured into water, and filtered to give 1-(cyclopropyl)-6-(2,4-dimethoxyphenyl)-4,5,7-trimethyl-6H-pyrrolo[3,4-d]pyridazine as a white solid: 1H NMR (CDCl3, 500 MHz) δ 7.03 (dd, 1H), 6.66-6.56 (m, 2H), 3.90 (s, 3H), 3.75 (s, 3H), 2.75 (s, 3H), 2.47 (s, 3H), 2.39 (quintet, 1H), 2.38 (s, 3H), 1.35-1.28 (m, 2H), 0.97 (dd, 2H); MS (ESI) 338 (M+H)+.

후처리

  1. extractionextracted with EtOAc
  2. washthe organic layer washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (10-25% EtOAc/hexanes)
  7. customto give the dione (MS (ESI) 342 (M +H)+)
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-a5038d784d844652bf6f32dfc5a1bbff
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465730B2

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