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3-Aminopyridine → 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine

HRID 2192967
ノート
印刷プレビュー

反応式

HRID 2192967 の反応式
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.[NH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.CC(C)([O-])C.[Na+].[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)[CH:14]=[CH:13][C:5]=1[C:6]([NH:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[N:7]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 100093-AminopyridineHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 593755141,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine

生成物 1

HCID 593755971-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine

試薬・触媒・溶媒 2

HCID 8028
Tetrahydrofuran
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

To a solution of 1,6-dichloro-9-(1-methyl-1H-pyrazol-4-yl)benzo[c]-1,6-naphthyridine (50 mg, 0.152 mmol) and 3-aminopyridine (14.30 mg, 0.152 mmol) in THF (1.5 mL), sodium tert-butoxide (43.8 mg, 0.456 mmol) was added. The reaction mixture was heated to 85° C. for 1 h. After cooling to room temperature, aqueous ammonium chloride (saturated) and ethyl acetate were added. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated under reduced pressure to afford 1-chloro-9-(1-methyl-1H-pyrazol-4-yl)-N-pyridin-3-ylbenzo[c]-1,6-naphthyridin-6-amine as a yellow solid. LRMS (APCI) calc'd for (C21H15ClN6) [M+H]+, 387.1; found 387.1.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-a22ab14a53d7405c8e25948fdc688ff7
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329722B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート