2-Chloro-4,6-difluoroaniline → HCID 59436014、化合物

HRID 1802487ノート

反応式

HRID 1802487 の反応式
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

参加物

7

反応物 4

HCID 27340832-Chloro-4,6-difluoroanilineHCID 23676156Sodium t-butoxideHCID 59436091HCID 59436091、化合物HCID 59436097HCID 59436097、化合物

生成物 2

HCID 59436014HCID 59436014、化合物HCID 59436106HCID 59436106、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d4a4e8bfa27e41ac9cc1803335175697
出典データセット
uspto-grants-2013_01
特許番号
US08349865B2

反応ノート

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