Propargyl bromide → HCID 58500414、化合物

HRID 1907140ノート

反応式

HRID 1907140 の反応式
[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][NH:13][N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[CH2:40](Br)[C:41]#[CH:42].CCOC(C)=O>C1COCC1.O>[CH:1]([NH:4][C:5]([C:7]1[C:15]2[C:11](=[CH:12][N:13]([CH2:42][C:41]#[CH:40])[N:14]=2)[CH:10]=[C:9]([CH3:16])[C:8]=1[NH:17][C:18]([C:20]1[N:21]([C:27]2[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[N:22]=[C:23]([O:25][CH3:26])[CH:24]=1)=[O:19])=[O:6])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 7842Propargyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178492656HCID 178492656、化合物

生成物 1

HCID 58500414HCID 58500414、化合物

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 6-{[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carbonyl]-amino}-5-methyl-2H-indazole-7-carboxylic acid isopropylamide (500 mg, 1.07 mmol) and K2CO3 (196 mg, 1.6 mmol) in THF (5 mL) was stirred for 1 hour at ambient temperature, and was treated with propargylbromide (120 μL, 1.6 mmol). The resulting reaction mixture was stirred for 24 hours at 60° C. AcOEt and water was added. The phases were separated. The aqueous layer was extracted with AcOEt. The organic layers were washed with water, combined, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3) afforded the title compound as a colorless crystalline solid. LC/MS: 506 (M+H)+, 528 (M+Na)+.

後処理

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 24 hours at 60° C
  3. customThe phases were separated
  4. extractionThe aqueous layer was extracted with AcOEt
  5. washThe organic layers were washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash-chromatography (SiO2, Toluene/AcOEt 7:3)

出典と根拠

ORDレコード
ord-da43438a95cc4a4d8ef3c3cc8a137e56
出典データセット
uspto-grants-2013_12
特許番号
US08598078B2

反応ノート

読み込み中…