2-Chloro-4,6-difluoroaniline → HCID 59436014, 화합물

HRID 1802487노트

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HRID 1802487 반응식
Cl[C:2]1[C:11]2[CH:12]=[CH:13][N:14]=[C:15]([O:16][CH2:17][CH3:18])[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.Cl[C:20]1[C:29]2[CH:30]=[CH:31][N:32]=[C:33]([Cl:34])[C:28]=2[C:27]2[C:22](=[CH:23][CH:24]=[N:25][CH:26]=2)[N:21]=1.[Cl:35][C:36]1[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[C:37]=1[NH2:38].CC(C)([O-])C.[Na+]>C1COCC1>[Cl:35][C:36]1[CH:42]=[C:41]([F:43])[CH:40]=[C:39]([F:44])[C:37]=1[NH:38][C:2]1[C:11]2[CH:12]=[CH:13][N:14]=[C:15]([O:16][CH2:17][CH3:18])[C:10]=2[C:9]2[C:4](=[CH:5][CH:6]=[N:7][CH:8]=2)[N:3]=1.[Cl:34][C:33]1[C:28]2[C:27]3[C:22](=[CH:23][CH:24]=[N:25][CH:26]=3)[N:21]=[C:20]([NH:38][C:37]3[C:39]([F:44])=[CH:40][C:41]([F:43])=[CH:42][C:36]=3[Cl:35])[C:29]=2[CH:30]=[CH:31][N:32]=1

참가 물질

7

반응물 4

HCID 27340832-Chloro-4,6-difluoroanilineHCID 23676156Sodium t-butoxideHCID 59436091HCID 59436091, 화합물HCID 59436097HCID 59436097, 화합물

생성물 2

HCID 59436014HCID 59436014, 화합물HCID 59436106HCID 59436106, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
85 °C

실험 절차

To a solution of 1.5:1 mixture of 6-chloro-10-ethoxypyrido[4,3-c]-1,6-naphthyridine and 6,10-dichloropyrido[4,3-c]-1,6-naphthyridine (1.5 g) in THF (25 mL) was added 2-chloro-4,6 difluoro aniline (945 mg, 5.78 mmol) and sodium tert-butoxide (1.65 g, 17 mmol). The solution was heated to 85° C. for 40 min then cooled to room temperature and extracted with EtOAc and brine. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified on silica gel (100% hexanes to 100% EtOAc, gradient elution) which provided N-(2-chloro-4,6-difluorophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine and 10-chloro-N-(2-chloro-4,6-difluorophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine.

후처리

  1. temperaturethen cooled to room temperature
  2. extractionextracted with EtOAc and brine
  3. dry with materialThe organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified on silica gel (100% hexanes to 100% EtOAc, gradient elution) which

출처 및 근거

ORD 기록
ord-d4a4e8bfa27e41ac9cc1803335175697
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349865B2

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