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

HRID 45737

반응식

HRID 45737 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][CH:20]=[C:19]([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:18]=1)(=[O:16])=[O:15].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])C.[O:43]([CH2:55][C:56]([O:58]N1C(=O)CCC1=O)=O)[CH2:44][C:45]([O:47]N1C(=O)CCC1=O)=O>CN(C=O)C>[O:43]([CH2:55][C:56]([NH:1][CH2:2][CH2:3][O:58][CH2:56][CH2:55][O:43][CH2:44][CH2:45][O:47][CH2:11][CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:40]2[C:32]3[C:42](=[C:28]([Cl:34])[CH:29]=[C:30]([Cl:33])[CH:31]=3)[CH2:41][N:38]([CH3:36])[CH2:39]2)[CH:18]=1)(=[O:16])=[O:15])=[O:58])[CH2:44][C:45]([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:22]=[CH:21][CH:20]=[C:19]([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:18]=1)(=[O:16])=[O:15])=[O:47]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 51340992Bis(2,5-dioxopyrrolidin-1-yl) 2,2'-oxydiacetate2회HCID 67458308N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2회

생성물 1

HCID 866723532,2'-oxybis(N-(2-(2-(2-(2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethoxy)ethoxy)ethoxy)ethyl)acetamide)수율 86.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Into a 50-mL round-bottom flask, was placed 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 28) (150 mg, 0.28 mmol, 1.00 equiv) in DMF (5 mL), triethylamine (56 mg, 0.55 mmol, 2.01 equiv) and bis(2,5-dioxopyrrolidin-1-yl) 2,2′-oxydiacetate (intermediate 178.1) (44 mg, 0.14 mmol, 0.49 equiv). The resulting solution was stirred overnight at room temperature, at which time the mixture was concentrated under vacuum. The crude product (150 mg) was purified by preparative HPLC with the following conditions: Column, C18 silica gel; mobile phase, methanol/water=0.05/100 increasing to methanol/water=90/100 within 19 min; Detector, UV 254 nm. This resulted in 72.4 mg (44%) of the title compound as a white solid. 1H-NMR (300 MHz, CD3OD, ppm): δ 7.79 (d, J=7.2 Hz, 2H), 7.71 (s, 2H), 7.49-7.58 (m, 4H), 7.36-7.37 (m, 2H), 6.82 (s, 2H), 4.39-4.44 (m, 2H), 4.06 (s, 4H), 3.80 (d, J=16.2 Hz, 2H), 3.65 (d, J=16.2 Hz, 2H), 3.55-3.61 (m, 16H), 3.43-3.52 (m, 12H), 3.02-3.08 (m, 6H), 2.65-2.70 (m, 2H), 2.49 (s, 6H). MS (m/z): 1190 [M+H]+

후처리

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationwas concentrated under vacuum
  3. customThe crude product (150 mg) was purified by preparative HPLC with the following conditions
  4. waitmobile phase, methanol/water=0.05/100 increasing to methanol/water=90/100 within 19 min

출처 및 근거

ORD 기록
ord-691ac873ee4c4f3c80f80ea5a40ee491
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541448B2

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