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 1242754

反応式

HRID 1242754 の反応式
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

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 4305447(2-nitrophenyl)methanesulfonyl ChlorideHCID 21935212HCID 21935212、化合物HCID 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

生成物 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))carboxamide収率 6.3%

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-38392a7ce06147c38eb4718a8abb51a6
出典データセット
uspto-grants-2006_10
特許番号
US07115607B2

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