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Pyridine → tert-Butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]ethyl}(methylsulfonyl)amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)-carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 228098
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HRID 228098 반응식
[CH3:1][S:2](NC1C=CC=CC=1N1CCN(C(OC(C)(C)C)=O)CC1)(=[O:4])=[O:3].[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]1[CH2:47][CH2:46][N:45]([C:48](=[O:78])[C@H:49]([NH:58][C:59]([C@@H:61]2[CH2:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH2:63][N:62]2[C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])=[O:60])[CH2:50][C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)[CH2:44][CH2:43]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].CS(Cl)(=O)=O.N1C=CC=CC=1>CN(C1C=CN=CC=1)C.C(Cl)CCl>[C:25]([O:29][C:30]([NH:32][CH2:33][CH2:34][N:35]([S:2]([CH3:1])(=[O:4])=[O:3])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[N:42]1[CH2:43][CH2:44][N:45]([C:48](=[O:78])[C@H:49]([NH:58][C:59]([C@@H:61]2[CH2:70][C:69]3[C:64](=[CH:65][CH:66]=[CH:67][CH:68]=3)[CH2:63][N:62]2[C:71]([O:73][C:74]([CH3:77])([CH3:76])[CH3:75])=[O:72])=[O:60])[CH2:50][C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)[CH2:46][CH2:47]1)=[O:31])([CH3:27])([CH3:28])[CH3:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21935212Tert-Butyl 4-(2-[(Methylsulfonyl)Amino]Phenyl)-PiperazinecarboxylateHCID 69073578tert-butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy) carbonylamino]ethyl}amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

생성물 1

HCID 86590296
tert-Butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]ethyl}(methylsulfonyl)amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)-carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 111,2-Dichloroethane용매

실험 절차

tert-Butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]ethyl}(methylsulfonyl)amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)-carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate was prepared according to the procedure for Preparation III using tert-butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy) carbonylamino]ethyl}amino)phenyl]piperazinyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step 1) (370 mg, 0.45 mmol), methanesulfonyl chloride (41 μl, 0.530 mmol), pyridine (40 μl, 0.495 mmol), DMAP (cat.), and ClCH2CH2Cl (15 mL). The crude material was purified by flash chromatography, (SiO2, 1:1 hexane:EtOAc) to afford the desired material (155 mg). MS (ESI, pos. ion) m/z: 839 (M+H), (ESI, neg. ion) m/z: 837 (M−H). Calc'd for C42H55ClN6O8S: 839.44.

후처리

  1. customThe crude material was purified by flash chromatography, (SiO2, 1:1 hexane:EtOAc)

출처 및 근거

ORD 기록
ord-0358bd10a40f4c57b6b9e4d3c5fc498b
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560460B2

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