Sulfuric Acid → Ethyl 3-carbamoyl-4-chloropyrrolo[1,2-b]pyridazine-6-carboxylate

HRID 1408905노트

반응식

HRID 1408905 반응식
[Cl:1][C:2]1[C:3]2[N:4]([CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=2)[N:5]=[CH:6][C:7]=1[C:8]#[N:9].[OH:18]S(O)(=O)=O>>[C:8]([C:7]1[CH:6]=[N:5][N:4]2[CH:10]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[C:3]2[C:2]=1[Cl:1])(=[O:18])[NH2:9]

참가 물질

3

반응물 2

HCID 1118Sulfuric AcidHCID 69326995Ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate

생성물 1

HCID 68290691Ethyl 3-carbamoyl-4-chloropyrrolo[1,2-b]pyridazine-6-carboxylate수율 70%

실험 절차

To a round bottom flask was added concentrated H2SO4 (100 mL) followed by ethyl 4-chloro-3-cyanopyrrolo[1,2-b]pyridazine-6-carboxylate (10 g, 40 mmol). The reaction was stirred at room temperature under nitrogen overnight. The reaction mixture was poured onto ice cold saturated sodium carbonate solution. The aqueous solution was extracted with EtOAc (4×) and the combined organic layer was concentrated to yield 7 g (70%) of the title compound as a yellow solid. HPLC (condition S): retention time=8.04 min. LCMS (condition A): m/z=268.0+ve. 1H NMR (400 MHz, CDCl3) δ ppm: 8.49 (1H, d, J=1.6 Hz), 8.40 (1H, s), 8.08 & 7.98 (1H, two br s), 7.12 (1H, d, J=1.6 Hz), 4.34 (2H, q, J=7.2 Hz), 1.34 (3H, t, J=7.2 Hz).

후처리

  1. additionThe reaction mixture was poured onto ice cold saturated sodium carbonate solution
  2. extractionThe aqueous solution was extracted with EtOAc (4×)
  3. concentrationthe combined organic layer was concentrated

출처 및 근거

ORD 기록
ord-842523514e384641a53b1e80f68a6164
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921368B2

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