Sodium Hydroxide → HCID 86661293, compound

HRID 1685031Notes

Reaction equation

HRID 1685031 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH:15]=O)[N:14]=1)=[O:8].[OH-].[Na+].[NH2:23][CH2:24][CH2:25][CH2:26][P:27](=[O:30])([OH:29])[OH:28].C([BH3-])#N.[Na+]>CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7](=[O:8])[NH:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][NH:23][CH2:24][CH2:25][CH2:26][P:27](=[O:28])([OH:30])[OH:29])[N:14]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 975873-Aminopropylphosphonic acidHCID 5003444Sodium cyanoborohydrideHCID 866227621-(3,4-Dichlorobenzyl)-3-(4-formylthiazol-2-yl)urea

Product 1

HCID 86661293HCID 86661293, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 887MethanolSolvent

Procedure

300 mg of 1-(3,4-dichlorobenzyl)-3-(4-formylthiazol-2-yl) urea was dissolved in 5 ml MeOH. 1.0 eq. of tetrabutylammonium bromide and 1.0 eq. of sodium hydroxide were added followed by addition of 1.0 eq. of 3-aminopropylphosphonic acid. To the mixture, 3.0 eq. of sodium cyanoborohydride was added and the reaction was stirred at room temp. overnight. The reaction mixture was loaded to reverse phase column and purified by HPLC to give 3-((2-(3-(3,4-dichlorobenzyl)ureido)thiazol-4-yl)methylamino)propylphosphonic acid.

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-34b40dc733d64cd18ec8505e2014876e
Source dataset
uspto-grants-2012_04
Patent number
US08148380B2

Reaction notes

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