1,2-Dichloroethane → n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide

HRID 228082노트

반응식

HRID 228082 반응식
Cl.[CH3:2][S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)(=[O:5])=[O:4].[CH3:19][C:20]([O:23][C:24]([NH:26][C@@H:27]([C:37]([OH:39])=[O:38])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[C:31]([Cl:36])[CH:30]=1)=[O:25])([CH3:22])[CH3:21].CC[N:42]([CH:46]([CH3:48])C)[CH:43]([CH3:45])C.C(Cl)CCl.[CH:53]1[CH:58]=N[C:56]2N(O)N=N[C:55]=2[CH:54]=1>CN(C=O)C>[Cl:36][C:31]1[CH:30]=[C:29]([CH2:28][C@@H:27]([NH:26][C:24]([O:23][C:20]([CH3:22])([CH3:21])[CH3:19])=[O:25])[C:37]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH2:14][CH2:15]2)=[O:38])[CH:34]=[CH:33][C:32]=1[Cl:35].[Cl:36][C:31]1[CH:30]=[C:29]([CH2:28][C@@H:27]([NH:26][C:24]([C@@H:46]2[CH2:48][C:56]3[C:45](=[CH:58][CH:53]=[CH:54][CH:55]=3)[CH2:43][NH:42]2)=[O:25])[C:37]([N:16]2[CH2:17][CH2:18][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH2:14][CH2:15]2)=[O:39])[CH:34]=[CH:33][C:32]=1[Cl:35]

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 70158113,4-Dichloro-N-((1,1-dimethylethoxy)carbonyl)-D-phenylalanineHCID 21283546N-(2-(Piperazin-1-yl)phenyl)methanesulfonamide hydrochloride

생성물 2

HCID 10282776n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide수율 113.3%HCID 21060073n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

N-[(1R)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide was prepared according to the procedure for Preparation XIX using (methylsulfonyl)(2-piperazinylphenyl)amine hydrochloride (800 mg, 2.8 mmol), N-Boc-D-3,4-dichlorophenylalanine (930 mg, 2.80 mmol) (Peptech), DIEA (480 μl, 2.80 mmol), EDC (1.66 g, 5.60 mmol), HOAT (400 mg, 3.0 mmol) and DMF (10 mL). The crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc) and concentrated in vacuo to afford the desired compound (1.0 g). MS (ESI, pos. ion) m/z: 571 (M+H), (ESI, neg. ion) m/z: 569 (M−H). Calc'd for C25H32Cl2N4O5S: 570.15.

후처리

  1. customThe crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc)
  2. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-965145ba56bd43d9bbff5519d303565f
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560460B2

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