Hydrochloric Acid → n-Propanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-amide

HRID 2252730Notes

Reaction equation

HRID 2252730 reaction equation
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[C:4]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=1.[K+].[CH2:25]([S:28]([NH-:31])(=[O:30])=[O:29])[CH2:26][CH3:27].Cl>CS(C)=O>[Cl:17][C:6]1[N:5]=[C:4]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=[C:2]([NH:31][S:28]([CH2:25][CH2:26][CH3:27])(=[O:30])=[O:29])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidineHCID 131726746n-Propanesulfonamide potassium salt

Product 1

HCID 86597592n-Propanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-[2,2']bipyrimidinyl-4-yl]-amideYield 99.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4,6-dichloro-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl (prepared as described in [6] and [11]) (1.74 g) in DMSO (5 ml) was added n-propanesulfonamide potassium salt (1.77 g). Stirring was continued for 10 days at rt. The reaction mixture was poured onto ice/water and acidified by 2N HCl. The precipitate was filtered off, washed with water and dried at HV to give n-propanesulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-[2,2′]bipyrimidinyl-4-yl]-amide (2.17 g) as a white powder. LC-MS: tR: 4.14, [M+H]+: 434.13.

Workup

  1. additionThe reaction mixture was poured onto ice/water
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried at HV

Sources & evidence

ORD record
ord-5cfca6df1cc344d48192ebb1efb7acf4
Source dataset
uspto-grants-2008_01
Patent number
US07323465B2

Reaction notes

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