2-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1) → 2-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine citrate

HRID 380329Notes

Reaction equation

HRID 380329 reaction equation
O.[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[Cl:15][C:16]1[N:17]=[C:18]([CH3:39])[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][N:29]([C:32]3[N:37]=[CH:36][C:35]([F:38])=[CH:34][N:33]=3)[CH2:28][CH2:27]2)[C:20]=1[Cl:21]>C(O)C>[C:2]([OH:14])(=[O:13])[CH2:3][C:4]([CH2:9][C:10]([OH:12])=[O:11])([C:6]([OH:8])=[O:7])[OH:5].[Cl:15][C:16]1[N:17]=[C:18]([CH3:39])[N:19]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]2[CH2:27][CH2:28][N:29]([C:32]3[N:37]=[CH:36][C:35]([F:38])=[CH:34][N:33]=3)[CH2:30][CH2:31]2)[C:20]=1[Cl:21]

Participants

4

Reactant 2

HCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 98083422-(4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine

Product 1

HCID 98083412-{4-[4-(4,5-Dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine citrateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.1 g (5.2 mmol) of citric acid monohydrate are added to a solution of 2 g (5.2 mol) of 2-(4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine in absolute ethanol. After a certain period of time, 2.72 g (91% yield) of 2-{4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl}-5-fluoropyrimidine citrate precipitate in the form of a solid with an M.p. of 151-153° C.

Sources & evidence

ORD record
ord-25dbb25a20914fcd861c5b5aaa3d0671
Source dataset
uspto-grants-2001_10
Patent number
US06303608B1

Reaction notes

Loading…