4-Methylmorpholine → 4-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acid

HRID 1423341노트

반응식

HRID 1423341 반응식
F[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.[CH:11]1([C:14]2[N:15]=[CH:16][NH:17][CH:18]=2)[CH2:13][CH2:12]1.CN1CCOCC1.C(#N)C.CO>CN(C)C=O.Cl>[CH:11]1([C:14]2[N:15]=[CH:16][N:17]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=3)[CH:18]=2)[CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 79724-MethylmorpholineHCID 183278054-Fluoropyridine-2-carboxylic acidHCID 21959252Acetonitrile methanolHCID 178420870HCID 178420870, 화합물

생성물 1

HCID 580356504-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acid수율 79.9%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 6228Dimethylformamide용매

반응 조건

온도
35 °C

실험 절차

A mixture of 4-fluoropicolinic acid (400 mg, 2.84 mmol) and 4-cyclopropyl-1H-imidazole (322 mg, 2.98 mmol) were dissolved in N,N-dimethylformamide, and N-methylmorpholine (0.36 ml, 3.28 mmol) was added. The reaction was warmed to 35° C., and stirred for 20 hours. The solvent was then removed under reduced pressure to afford a viscous oily residue. This residue was dissolved in 1N hydrochloric acid (5 mL), and the aqueous layer was extracted with ethyl acetate (2×5 mL). The aqueous layer was concentrated under reduced pressure to afford a yellow solid. To this residue was added 5 mL of acetonitrile/methanol (20:1) and the mixture was sonicated to afford a fine suspension of solids. The solids were collected by filtration, washed several times with acetonitrile, and dried on the filter funnel. The yellow solids were collected to afford 520 mg (69% yield) of 4-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acid as the hydrochloride salt. M+1=230.1

후처리

  1. customThe solvent was then removed under reduced pressure
  2. customto afford a viscous oily residue
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×5 mL)
  4. concentrationThe aqueous layer was concentrated under reduced pressure
  5. customto afford a yellow solid
  6. customthe mixture was sonicated
  7. customto afford
  8. additiona fine suspension of solids
  9. filtrationThe solids were collected by filtration
  10. washwashed several times with acetonitrile
  11. customdried on the filter funnel
  12. customThe yellow solids were collected

출처 및 근거

ORD 기록
ord-d199db2781874f89a06bff4bcce8474a
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08927582B2

반응 노트

불러오는 중…