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

HRID 7473노트

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HRID 7473 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

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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-86f02a2df9b34f72ae5e90ef9abd5f91
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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