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

HRID 1057328

반응식

HRID 1057328 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

반응 조건

온도
110 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-178250ee66dd43a8905c5ff52b09b169
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06514971B1

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