Triphenylphosphine → N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

HRID 45718

반응식

HRID 45718 반응식
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]2[C:34]3[C:29](=[C:30]([Cl:36])[CH:31]=[C:32]([Cl:35])[CH:33]=3)[CH2:28][N:27]([CH3:37])[CH2:26]2)[CH:20]=1)(=[O:18])=[O:17])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[NH2:1][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]2[C:34]3[C:29](=[C:30]([Cl:36])[CH:31]=[C:32]([Cl:35])[CH:33]=3)[CH2:28][N:27]([CH3:37])[CH2:26]2)[CH:20]=1)(=[O:18])=[O:17]

참가 물질

4

반응물 2

HCID 11776TriphenylphosphineHCID 86672333N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

생성물 1

HCID 67458308N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide수율 67.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To N-(2-(2-(2-(2-azidoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (1.8 g, 3.26 mmol, 1.00 equiv) in THF (30 mL) was added triphenylphosphine (2.6 g, 9.91 mmol, 3.04 equiv). The resulting solution was stirred overnight at room temperature and then concentrated under vacuum. The crude product (5.0 g) was purified by Flash-Prep-HPLC with the following conditions: Column, silica gel; mobile phase, methanol:water=1:9 increasing to methanol:water=9:1 within 30 min; Detector, UV 254 nm. 1.2 g product was obtained. This resulted in 1.2 g (64%) of N-(2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide as yellow oil.

후처리

  1. concentrationconcentrated under vacuum
  2. customThe crude product (5.0 g) was purified by Flash-Prep-HPLC with the following conditions
  3. waitmobile phase, methanol:water=1:9 increasing to methanol:water=9:1 within 30 min

출처 및 근거

ORD 기록
ord-7e16593862ae42c8be45699019351411
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541448B2

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