Methyl 3-amino-4-methylbenzoate → Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

HRID 1802466노트

반응식

HRID 1802466 반응식
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2Cl.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23].CC(C)([O-])C.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2[NH:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23]

참가 물질

5

반응물 3

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23676156Sodium t-butoxideHCID 594361181,5-Dichloro-9-fluorobenzo[c]-2,6-naphthyridine

생성물 1

HCID 59436117Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthytidine (Example 1, Step 5) (500 mg, 1.87 mmol) and methyl 3-amino-4-methylbenzoate (340 mg, 2.06 mmol) in THF (9.3 mL) was added sodium tert-butoxide (396 mg, 4.12 mmol). The reaction stirred at room temperature for ten minutes and was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-30% EtOAc/heptane) afforded the title compound.

후처리

  1. customwas then quenched by the addition of sat. aq. NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (0-30% EtOAc/heptane)

출처 및 근거

ORD 기록
ord-13067376039147abb3299da62522dbba
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349865B2

반응 노트

불러오는 중…