Ethyl 2-((diethoxyphosphoryl)methylamino)acetate → ethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-N-((diethoxyphosphoryl)methyl)phenylsulfonamido)acetate

HRID 1470087Notes

Reaction equation

HRID 1470087 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][NH:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([Cl:28])[CH:27]=1)[CH2:24][N:23]([CH3:29])[CH2:22][CH:21]2[C:30]1[CH:31]=[C:32]([S:36](Cl)(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1>N1C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[C:26]([Cl:28])[CH:27]=1)[CH2:24][N:23]([CH3:29])[CH2:22][CH:21]2[C:30]1[CH:31]=[C:32]([S:36]([N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9][P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])(=[O:38])=[O:37])[CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 4490933Ethyl 2-((diethoxyphosphoryl)methylamino)acetateHCID 866723303-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride

Product 1

HCID 86672332ethyl 2-(3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-N-((diethoxyphosphoryl)methyl)phenylsulfonamido)acetateYield 26.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of ethyl 2-((diethoxyphosphoryl)methylamino)acetate (320 mg, 1.26 mmol, 1.00 equiv) in pyridine (10 mL). 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzene-1-sulfonyl chloride (500 mg, 1.28 mmol, 1.01 equiv) was added and the resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The crude product (400 mg) was purified by preparative HPLC to give 200 mg (24%) of the title compound as a TFA salt.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThe crude product (400 mg) was purified by preparative HPLC

Sources & evidence

ORD record
ord-49eb447b35a24a5095711f7950a3c402
Source dataset
uspto-grants-2015_04
Patent number
US09006281B2

Reaction notes

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