Chloroacetyl chloride → HCID 57794564, 화합물

HRID 2099377노트

반응식

HRID 2099377 반응식
Cl[CH2:2][C:3](Cl)=[O:4].Cl.Cl.[Cl:8][C:9]1[C:10]([F:35])=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][C@H:29]4[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]4)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1.C(N(C(C)C)CC)(C)C.[CH3:45][N:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>C(Cl)Cl>[Cl:8][C:9]1[C:10]([F:35])=[C:11]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][C:22]([O:28][C@H:29]4[CH2:34][CH2:33][CH2:32][N:31]([C:3](=[O:4])[CH2:2][N:49]5[CH2:50][CH2:51][N:46]([CH3:45])[CH2:47][CH2:48]5)[CH2:30]4)=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=[CH:18][N:17]=2)[CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 68908613HCID 68908613, 화합물

생성물 1

HCID 57794564HCID 57794564, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Chloroacetyl chloride (47 μl) was added to a solution of N-(3-chloro-2-fluorophenyl)-6-methoxy-7-[(3S)-piperidin-3-yloxy]quinazolin-4-amine dihydrochloride (250 mg) and diisopropylethylamine (373 μl) in methylene chloride (10 ml) and the mixture was stirred at ambient temperature for 1 hour. 1-Methylpiperazine (228 mg) was added, and the solution stirred for 1 hour before being washed with aqueous sodium hydroxide (2M, 10 ml) and water (10 ml). The organics were then purified by flash column chromatography eluting with methylene chloride/7N ammonia solution in methanol (97/3) to give a foam. This was re-precipitated by stirring in diethyl ether (20 ml) to give the title product as a white solid (0.135 g); 1H NMR Spectrum: (DMSO d6) 1.42-1.67 (m, 1H), 1.70-1.95 (m, 2H), 1.98-2.48 (m, 9H), 2.18 (s, 3H), 2.82-3.05 (m, 1H), 3.20-4.02 (m, 8H), 4.68 (m, 1H,), 7.30 (m, 1H), 7.34 (s, 1H), 7.44-7.60 (m, 2H), 7.82 (m, 1H), 8.38 (s, 1H), 9.64 (m, 1H); Mass Spectrum: (M+H)+ 543; melting point 120 to 121° C.

후처리

  1. stirringthe solution stirred for 1 hour
  2. washbefore being washed with aqueous sodium hydroxide (2M, 10 ml) and water (10 ml)
  3. customThe organics were then purified by flash column chromatography
  4. washeluting with methylene chloride/7N ammonia solution in methanol (97/3)
  5. customto give a foam
  6. customThis was re-precipitated
  7. stirringby stirring in diethyl ether (20 ml)

출처 및 근거

ORD 기록
ord-e474d81da0474e5aa2f65c8294895fd4
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569577B2

반응 노트

불러오는 중…