Diethyl p-aminobenzylphosphonate → 4-(3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)benzylphosphonic acid

HRID 870135Notes

Reaction equation

HRID 870135 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([S:20]([NH:23][CH2:24][CH2:25]P(=O)(O)O)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1.NC1C=[CH:44][C:34]([CH2:35][P:36](=[O:43])([O:40]CC)[O:37]CC)=[CH:33][CH:32]=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[C:16]([S:20]([NH:23][C:24]2[CH:25]=[CH:44][C:34]([CH2:35][P:36](=[O:37])([OH:43])[OH:40])=[CH:33][CH:32]=2)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 88358Diethyl p-aminobenzylphosphonate2×HCID 674602442-(3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)ethylphosphonic acid

Product 1

HCID 674600734-(3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylsulfonamido)benzylphosphonic acid

Procedure

Compound 3 was prepared in an analogous manner to that of Compound 1 using diethyl 4-aminobenzylphosphonate (Intermediate 3.2) as the amine. 1H-NMR (300 MHz, CD3OD, ppm): 7.89 (d, J=7.8 Hz, 1H), 7.61˜7.66 (m, 1H), 7.52˜7.54 (m, 2H), 7.21˜7.20 (m, 2H), 7.11 (s, 1H), 6.95 (d, J=8.1 Hz, 2H), 6.73 (s, 1H), 4.51˜4.59 (m, 3H), 3.33 (s, 1H), 3.03˜2.89 (m, 6H). MS (ES, m/z): 541 [M+H]+.

Sources & evidence

ORD record
ord-c5816b14dc104f6bb70fa75ef5d3a13f
Source dataset
uspto-grants-2015_03
Patent number
US08969377B2

Reaction notes

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