1,4-Dimercapto-2,3-butanediol → 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea

HRID 1035755

Reaction equation

HRID 1035755 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([CH3:8])[CH2:5][N:4]([CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([S:24]C#N)[CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:13])[CH2:3]1.SCC(C(CS)O)O>P([O-])(O)(O)=O.[K+]>[CH3:8][C@H:6]1[O:7][C@@H:2]([CH3:1])[CH2:3][N:4]([CH2:9][CH2:10][NH:11][C:12]([NH:14][C:15]2[S:16][C:17]3[CH:23]=[C:22]([SH:24])[CH:21]=[CH:20][C:18]=3[N:19]=2)=[O:13])[CH2:5]1

Participants

4

Reactant 2

HCID 190011,4-Dimercapto-2,3-butanediolHCID 866478792-[({2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}carbamoyl)amino]-1,3-benzothiazol-6-yl thiocyanate

Product 1

HCID 866478781-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)ureaYield 99.6%

Reagents, catalysts & solvents 1

HCID 516951Monobasic potassium phosphateCatalyst

Procedure

The 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea was prepared according to the method described in Example 1b, but using 640 mg of 2-[({2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}carbamoyl)amino]-1,3-benzothiazol-6-yl thiocyanate, 7 mg of potassium dihydrogen phosphate and 729 mg of DL-dithiothreitol. 597 mg of 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea are thus obtained in the form of a white solid, the characteristics of which are as follows:

Workup

  1. customThe 1-{2-[(2R,6S)-2,6-dimethylmorpholin-4-yl]ethyl}-3-(6-sulphanyl-1,3-benzothiazol-2-yl)urea was prepared

Sources & evidence

ORD record
ord-cc83682082eb4d0f86adc70454bb1041
Source dataset
uspto-grants-2013_10
Patent number
US08546393B2

Linked notes

Loading…