Morpholine → 6-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole

HRID 1398572노트

반응식

HRID 1398572 반응식
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=O)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:13])=[N:7][NH:8]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8083MorpholineHCID 682631,1'-CarbonyldiimidazoleHCID 247280286-Bromo-1H-indazole-3-carboxylic acid

생성물 1

HCID 681818546-bromo-3-[(morpholin-4-yl)carbonyl]-1H-indazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

To a solution of 6-bromo-1H-indazole-3-carboxylic acid (500 mg, 2.07 mmol) in DMF (10 mL) was added CDI (403.62 mg, 2.49 mmol) and the reaction mixture stirred at 45° C. for 40 minutes. Morpholine (0.36 ml, 4.16 mmol) was then added and the reaction mixture stirred at RT. The reaction mixture was quenched by diluting with water. The product was extracted into EtOAc (×2) and the combined organic extracts were then washed with water and brine and dried (Na2SO4), filtered and concentrated in vacuo to give the crude (78% pure) title compound: 1H NMR (500 MHz, DMSO) delta 3.58-3.79 (6H, m), 3.96-4.13 (2H, m), 7.36 (1H, dd, J=8.59, 1.66 Hz), 7.86 (1H, d, J=1.10 Hz), 7.93 (1H, s), 13.66 (1H, br. s.); LC-MS: m/z=+311.70 (M+H)+.

후처리

  1. stirringthe reaction mixture stirred at RT
  2. customThe reaction mixture was quenched
  3. additionby diluting with water
  4. extractionThe product was extracted into EtOAc (×2)
  5. washthe combined organic extracts were then washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-6a77fbb8c287432299f1dcd7d3ba975a
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901313B2

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