Triethylamine → 2,2'-oxybis(N-(2-(2-(2-(2-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)acetamide)

HRID 870234

반응식

HRID 870234 반응식
[NH2:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[C:32]3[C:27](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=3)[CH2:26][N:25]([CH3:35])[CH2:24]2)=[CH:19][CH:18]=1)(=[O:16])=[O:15].[O:36]([CH2:48][C:49]([O:51]N1C(=O)CCC1=O)=O)[CH2:37][C:38]([O:40]N1C(=O)CCC1=O)=O.[CH2:59]([N:61]([CH2:64][CH3:65])[CH2:62][CH3:63])C>CN(C=O)C>[O:36]([CH2:48][C:49]([NH:1][CH2:2][CH2:3][O:51][CH2:49][CH2:48][O:36][CH2:37][CH2:38][O:40][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([CH:63]2[C:32]3[C:65](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=3)[CH2:64][N:61]([CH3:59])[CH2:62]2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:51])[CH2:37][C:38]([NH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[C:32]3[C:27](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=3)[CH2:26][N:25]([CH3:35])[CH2:24]2)=[CH:21][CH:22]=1)(=[O:16])=[O:15])=[O:40]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 46843244N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2회HCID 51340992Bis(2,5-dioxopyrrolidin-1-yl) 2,2'-oxydiacetate2회

생성물 1

HCID 866723582,2'-oxybis(N-(2-(2-(2-(2-(4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)acetamide)수율 73.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 82) (200 mg, 0.37 mmol) in DMF (2 mL) was added bis(2,5-dioxopyrrolidin-1-yl) 2,2′-oxydiacetate (intermediate 178.1) (60 mg) and triethylamine (184 mg). The resulting solution was stirred for 2 h at room temperature at which point LCMS indicated complete conversion. The mixture was concentrated under vacuum and the crude product was purified by Prep-HPLC with acetonitrile:water (0.05% CF3COOH) (25%-35%). This resulted in 79.6 mg (31%) of the title compound as a TFA salt. 1H-NMR (300 MHz, CD3OD, ppm): 7.94-7.91 (m, 4H), 7.58-7.57 (m, 2H), 7.51-7.48 (m, 4H), 6.88 (m, 2H), 4.82-4.74 (m, 4H), 4.52-4.47 (m, 2H), 4.06 (m, 4H), 3.90 (m, 2H), 3.64-3.42 (m, 34H), 3.15-3.13 (s, 6H), 3.11-3.09 (m, 4H). LC-MS (ES, m/z): 596 [(M+2H)/2]+.

후처리

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe crude product was purified by Prep-HPLC with acetonitrile

출처 및 근거

ORD 기록
ord-42b0cba339304481b92211d2cbf8fc8c
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969377B2

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