Diisopropylethylamine → N-(32-azido-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide

HRID 870238Notes

Reaction equation

HRID 870238 reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][NH2:36])=[N+:2]=[N-:3].[Cl:37][C:38]1[CH:39]=[C:40]2[C:45](=[C:46]([Cl:48])[CH:47]=1)[CH2:44][N:43]([CH3:49])[CH2:42][CH:41]2[C:50]1[CH:51]=[C:52]([S:56](Cl)(=[O:58])=[O:57])[CH:53]=[CH:54][CH:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[N:1]([CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][CH2:25][CH2:26][O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][NH:36][S:56]([C:52]1[CH:53]=[CH:54][CH:55]=[C:50]([CH:41]2[C:40]3[C:45](=[C:46]([Cl:48])[CH:47]=[C:38]([Cl:37])[CH:39]=3)[CH2:44][N:43]([CH3:49])[CH2:42]2)[CH:51]=1)(=[O:58])=[O:57])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4093966Azido-PEG-amine (n=10)HCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 86672362N-(32-azido-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 32-azido-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontan-1-amine (436.9 mg, 0.777 mmol) in dry DMF (3.5 mL) under N2 was cooled to 0° C. A solution of 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (300 mg, 0.706 mmol) and DIEA (273.2 mg, 2.118 mmol) in DMF (3 mL) was added dropwise. After 60 minutes LCMS indicated complete conversion and the solvent was removed to give N-(32-azido-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (620 mg) as a yellow oil which was used without further purification.

Workup

  1. customthe solvent was removed

Sources & evidence

ORD record
ord-fd806bb5e1274890852ce9054d9b7079
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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