Ethylene Glycol → HCID 178489612, compound

HRID 1871596Notes

Reaction equation

HRID 1871596 reaction equation
[OH-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH:11]=2)[N:7]=[C:6]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][N:26]=2)(=[O:24])=[O:23])[C:5]=1[O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42].[CH2:43]([OH:46])[CH2:44][OH:45].Cl>O>[OH:45][CH2:44][CH2:43][O:46][C:4]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([C:16]3[NH:20][N:19]=[N:18][N:17]=3)[CH:11]=2)[N:7]=[C:6]([NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][N:26]=2)(=[O:24])=[O:23])[C:5]=1[O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[O:41][CH3:42]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178489607HCID 178489607, compound

Product 1

HCID 178489612HCID 178489612, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

6.2 g of sodium hydroxide were added to 15 g (26 mmol) of 5-isopropyl-pyridine-2-sulfonic acid [6-chloro-5-(2-methoxy-phenoxy)-2-[2-(1H-tetrazole-5-yl)-pyridine-4-yl]-pyrimidine-4-yl]-amid and 75 ml of ethylene glycol. The mixture was heated to 85° C. for 5 hr. Then 55 ml of de-ionized water were added and thereafter 55 ml of 3 N hydrochloric acid were added dropwise. The mixture was allowed to cool down to 20° C. and was stirred for 1 hr. The solid was filtered off and dried at 70° C., 2000 Pa for 18 hr. There were obtained 16.2 g (103%) of 5-isopropyl-pyridine-2-sulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-[2-(1H-tetrazole-5-yl)-pyridine-4-yl]-pyrimidine-4-yl]-amide with a HPLC purity of 92% (w/w). 80 ml of dioxane and 80 ml of ethanol were added to this solid. At a temperature of 60° C., gaseous ammonia was introduced into the liquid until pH=9 to 10. The resulting suspension was allowed to cool down to 20° C. and was stirred at 20° C. for 20 hr and thereafter at 0° C. for 2.5 hr. Then the solid was filtered off and dried at 70° C., 2000 Pa for 18 hr. There were obtained 14.2 g of mono ammonium salt with a HPLC purity of 96.2% (w/w). The solid was heated (reflux) in 70 ml of methanol, cooled down slowly to 20° C. and stirred at 20° C. for 19 hr and thereafter at 0° C. for 2 hr. Then the solid was filtered off and dried at 70° C., 2000 Pa for 19 hr. There were obtained 11.5 g (66% of theory) of 5-isopropyl-pyridine-2-sulfonic acid [6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-[2-(1H-tetrazole-5-yl)-pyridine-4-yl]-pyrimidine-4-yl]-amide sodium salt (1:2) with a HPLC purity of 98.6% (w/w).

Workup

  1. temperatureto cool down to 20° C.
  2. filtrationThe solid was filtered off
  3. customdried at 70° C.
  4. wait2000 Pa for 18 hr

Sources & evidence

ORD record
ord-eb2d1d6ebbc44182914a7b46061f90a2
Source dataset
uspto-grants-2000_08
Patent number
US06103902

Reaction notes

Loading…