Hydrochloric Acid → n-((1r)-1-[(4-Chlorophenyl)methyl]-2-{4-[2-({[(2-nitrophenyl)methyl]sulfonyl}amino)phenyl]piperazinyl}-2-oxoethyl)((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide

HRID 228102

반응식

HRID 228102 반응식
CS(NC1C=CC=CC=1N1CCN(C(OC(C)(C)C)=O)CC1)(=O)=O.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][N:35]([C:38](=[O:68])[C@H:39]([NH:48][C:49]([C@@H:51]2[CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:53][N:52]2C(OC(C)(C)C)=O)=[O:50])[CH2:40][C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[CH2:34][CH2:33]1.N1C=CC=CC=1.[N+:75]([C:78]1[CH:83]=[CH:82][CH:81]=[CH:80][C:79]=1[CH2:84][S:85](Cl)(=[O:87])=[O:86])([O-:77])=[O:76].Cl>C(Cl)CCl.CCOC(C)=O>[Cl:47][C:44]1[CH:43]=[CH:42][C:41]([CH2:40][C@@H:39]([NH:48][C:49]([C@@H:51]2[CH2:60][C:59]3[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=3)[CH2:53][NH:52]2)=[O:50])[C:38]([N:35]2[CH2:36][CH2:37][N:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[NH:25][S:85]([CH2:84][C:79]3[CH:80]=[CH:81][CH:82]=[CH:83][C:78]=3[N+:75]([O-:77])=[O:76])(=[O:86])=[O:87])[CH2:33][CH2:34]2)=[O:68])=[CH:46][CH:45]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4305447(2-nitrophenyl)methanesulfonyl ChlorideHCID 21935212HCID 21935212, 화합물HCID 58714321tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

생성물 1

HCID 10283676n-((1r)-1-[(4-Chlorophenyl)methyl]-2-{4-[2-({[(2-nitrophenyl)methyl]sulfonyl}amino)phenyl]piperazinyl}-2-oxoethyl)((3s)(3-1,2,3,4-tetrahydroisoquinolyl))carboxamide수율 6.3%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

Following the procedure for the synthesis of Preparation III, the title compound was prepared from tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperazinyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Preparation IX) (250 mg, 0.40 mmol) in ClCH2CH2Cl (1.5 mL), pyridine (0.040 mL, 0.44 mmol), and 2-nitro-α-toluenesulfonyl chloride (Aldrich) (104 mg, 0.44 mmol). The crude was treated with a soln of HCl satd EtOAc, which resulted in the precipitation of the salt. This material was collected by filtration, dried in vacuo, and recrystallized from MeOH to afford the product as the HCl salt (18 mg). MS (ESI, pos. ion) m/z: 717 (M+H). Calc'd for C36H37ClN6O4S: 716.

후처리

  1. customresulted in the precipitation of the salt
  2. filtrationThis material was collected by filtration
  3. customdried in vacuo
  4. customrecrystallized from MeOH

출처 및 근거

ORD 기록
ord-d055766315c44961a0fcafa0d8b414b5
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560460B2

연결된 노트

불러오는 중…