Dichloromethane → HCID 10019969、化合物

HRID 2375376ノート

反応式

HRID 2375376 の反応式
[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

参加物

10

反応物 5

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

生成物 1

HCID 10019969HCID 10019969、化合物

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-a5038d784d844652bf6f32dfc5a1bbff
出典データセット
uspto-grants-2008_12
特許番号
US07465730B2

反応ノート

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