Hydrochloric Acid → 4-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

HRID 2205762ノート

反応式

HRID 2205762 の反応式
[N:1]([O-])=O.[Na+].[ClH:5].C(OC([N:11]1[C:15]([NH2:16])=[C:14]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:13]=[N:12]1)C)C.C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:5][C:17]1[C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:1][N:16]=[C:15]2[NH:11][N:12]=[CH:13][C:14]=12

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 867172621-(1-ethoxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-amine

生成物 1

HCID 867172634-chloro-5-phenyl-1H-pyrazolo[3,4-c]pyridazine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Sodium nitrite (4.3 g, 63 mmol) was added to conc. HCl (314 mL) at −15° C. and stirred for 10 min. 1-(1-ethoxyethyl)-4-(phenylethynyl)-1H-pyrazol-5-amine (3 g, 31.4 mmol) was added and the mixture stirred at −10° C. for 10 min and room temperature for 1 d. The reaction mixture was cooled to 0° C. and CH2Cl2 (250 mL) was added. Under vigorous stirring, Na2CO3 (160 g) was added carefully followed by sat. aq. NaHCO3 solution over a period of 2 h until the pH was 7 and there was no more foaming on further addition of base. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica gel, iso-hexanes/diethyl ether 1:0 to 0:1) yielding the title compound as a solid (3.43 g).

後処理

  1. stirringthe mixture stirred at −10° C. for 10 min and room temperature for 1 d
  2. additionon further addition of base
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica gel, iso-hexanes/diethyl ether 1:0 to 0:1)

出典と根拠

ORDレコード
ord-da8b83be8bf842129eef32a36bbb7db1
出典データセット
uspto-grants-2016_06
特許番号
US09371332B2

反応ノート

読み込み中…