2,6-Dichloro-4-iodobenzenamine → HCID 59436035、化合物

HRID 1802494ノート

反応式

HRID 1802494 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]([I:43])[CH:40]=[C:39]([Cl:44])[C:37]=1[NH2:38].CC(C)([O-])C.[Na+]>C1COCC1>[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:36]([Cl:35])=[CH:42][C:41]([I:43])=[CH:40][C:39]=3[Cl:44])[C:29]=2[CH:30]=[CH:31][N:32]=1.[Cl:35][C:36]1[CH:42]=[C:41]([I:43])[CH:40]=[C:39]([Cl: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

参加物

7

反応物 4

HCID 127702,6-Dichloro-4-iodobenzenamineHCID 23676156Sodium t-butoxideHCID 59436091HCID 59436091、化合物HCID 59436097HCID 59436097、化合物

生成物 2

HCID 59436035HCID 59436035、化合物HCID 86643799HCID 86643799、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 mixture of 6-chloro-10-ethoxypyrido[4,3-c]-1,6-naphthyridine (Example 133, Step 3) (200 mg, 0.770 mmol) and 6,10-dichloropyrido[4,3-c]-1,6-naphthyridine (Example 133, Step 3)(193, 0.770 mmol) in THF (12 mL) were added 2,6-dichloro-4-iodoaniline (443 mg, 1.54 mmol) and sodium tert-butoxide (444 mg, 4.62 mmol) and the mixture was heated to 85° C. for 1 hr. After cooling to room temperature, the mixture was extracted with EtOAc. The organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. Column chromatography (100% hexane to 100% EtOAc) provided 10-chloro-N-(2,6-dichloro-4-iodophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine and N-(2,6-dichloro-4-iodophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine. Most instances 10-chloro-N-(2,6-dichloro-4-iodophenyl)pyrido[4,3-c]-1,6-naphthyridin-6-amine and N-(2,6-dichloro-4-iodophenyl)-10-ethoxypyrido[4,3-c]-1,6-naphthyridin-6-amine were carried on as a mixture, however, the mixtures can be separated and carried on separately. This mixture (282 mg) was taken up in methanol (5 mL) and 25% sodium methoxide (3 mL) and heated at 100° C. for 1 hr. After cooling to room temperature, the solution was concentrated and then taken up in EtOAc and washed with water. The organic layers were dried with MgSO4, filtered, and concentrated to afford the title compounds.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc
  3. dry with materialThe organic layers were dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-d7d72e4031ce4e0fbe7b053a1d59b526
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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