Acetic Anhydride → 4-(5-Acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxycinnoline

HRID 1057328ノート

反応式

HRID 1057328 の反応式
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH2:8]([O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:26][C:27]3C=C(O)[C:30]([Cl:34])=[CH:29][C:28]=3[F:35])=[CH:21][N:22]=[N:23]2)=[CH:18][C:17]=1[O:36][CH3:37])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:5]([O:4][C:1]1[C:30]([Cl:34])=[CH:29][C:28]([F:35])=[C:27]([CH:2]=1)[NH:26][C:20]1[C:19]2[C:24](=[CH:25][C:16]([O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:17]([O:36][CH3:37])[CH:18]=2)[N:23]=[N:22][CH:21]=1)(=[O:7])[CH3:6]

参加物

5

反応物 2

HCID 7918Acetic AnhydrideHCID 219910477-Benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline

生成物 1

HCID 219910324-(5-Acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxycinnoline

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
110 °C

実験手順

Acetic anhydride (920 μl, 9.7 mmol) and 4-dimethylaminopyridine (80 mg, 0.65 mmol) were added to a suspension of 7-benzyloxy-4-(4-chloro-2-fluoro-5-hydroxyanilino)-6-methoxycinnoline (3 g, 6.5 mmol), (prepared as described in Example 6), in pyridine (50 ml). After heating at 110° C. for 25 minutes, the solid was filtered off, washed with water and ether and dried under vacuum. The solid was suspended in 2M ethereal hydrogen chloride and the volatiles removed by evaporation to give 4-(5-acetoxy-4-chloro-2-fluoroanilino)-7-benzyloxy-6-methoxycinnoline as the hydrochloride salt (yellow solid. 3.1 g, 94%).

後処理

  1. filtrationthe solid was filtered off
  2. washwashed with water and ether
  3. customdried under vacuum
  4. customthe volatiles removed by evaporation

出典と根拠

ORDレコード
ord-178250ee66dd43a8905c5ff52b09b169
出典データセット
uspto-grants-2003_02
特許番号
US06514971B1

反応ノート

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