N,N-Dimethylethylenediamine → HCID 73442306, compound

HRID 1049850Notes

Reaction equation

HRID 1049850 reaction equation
Br[C:2]1[NH:21][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]3[CH:20]=[CH:19][C:14]4[NH:15][C:16](=[O:18])[S:17][C:13]=4[CH:12]=3)[C:4]=2[CH:3]=1.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.[Na+].CN(C)CCN>CS(C)=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([C:2]2[NH:21][C:5]3[N:6]=[CH:7][N:8]=[C:9]([NH:10][C:11]4[CH:20]=[CH:19][C:14]5[NH:15][C:16](=[O:18])[S:17][C:13]=5[CH:12]=4)[C:4]=3[CH:3]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 66053N,N-DimethylethylenediamineHCID 23664783Sodium 4-chlorobenzenesulfinateHCID 73442187HCID 73442187, compound

Product 1

HCID 73442306HCID 73442306, compoundYield 3.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture comprising 50 mg (138 μmol) 6-[(6-bromo-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]-1,3-benzothiazol-2(3H)-one (prepared according to example 8), 0.6 mL dimethyl sulfoxide, 109.7 mg sodium 4-chlorobenzenesulfinate, 7.7 mg (mu-benzene-1,2,3,4-tetrayl-1 kappa2C1,C2:2kappa2C3,C4)[bis(trifluoromethanesulfonatato-kappaO)]dicopper, 2.97 μL N,N-dimethylethane-1,2-diamine was heated at 120° C. for 2 hours to give after chromatography 2.2 mg (3%) of the title compound.

Sources & evidence

ORD record
ord-f9c0f623e2b54d199107c7717d1b6c46
Source dataset
uspto-grants-2016_07
Patent number
US09382255B2

Reaction notes

Loading…