Hydrochloric Acid → HCID 178489607, compound

HRID 1871595Notes

Reaction equation

HRID 1871595 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH:16][NH2:17])=[NH:15])[CH:9]=2)[N:5]=[C:4]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])[C:3]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39].C[N:41](C)C=O.Cl.N([O-])=O.[Na+]>O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]3[NH:15][N:41]=[N:17][N:16]=3)[CH:9]=2)[N:5]=[C:4]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([CH:28]([CH3:30])[CH3:29])=[CH:24][N:23]=2)(=[O:21])=[O:20])[C:3]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 23668193Sodium NitriteHCID 178489609HCID 178489609, compound

Product 1

HCID 178489607HCID 178489607, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
20 °C

Procedure

20 g (35 mmol) of 5-isopropyl-pyridine-2-sulfonic acid [6-chloro-2-[2-(hydrazino-imino-methyl)-pyridine-4-yl]-5-(2-methoxy-phenoxy)-pyrimidine-4-yl]-amide were added to 160 ml of N,N-dimethyl formamide. The solution was kept at 15° C. to 20° C. and 23 ml of 6 N aqueous hydrochloric acid were added, followed by addition of a solution containing 4.8 g (7 mmol) of sodium nitrite in 20 ml de-ionized water within 10 min. The mixture was stirred at 20° C. for 1 hr, then 140 ml of de-ionized water were added and the suspension was stirred at 0° C. for 1 hr. The solid was filtered, firstly washed with 80 ml of de-ionized water and thereafter with 80 ml of t-butylmethylether. Then the solid was dried at 70° C. and 2000 Pa for 16 hr. The crude product (23.4 g) was taken up with 117 ml of tetrahydrofuran for 1 hr. After filtration at 0° C. the crystallized product was washed with 25 ml of t-butylmethylether and was then dried at 70° C., 2000 Pa for 16 hr. There were obtained 17.3 g (84% of theory) 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]-amide with a HPLC purity of 91.1% (w/w).

Workup

  1. customwas kept at 15° C. to 20° C.
  2. additionfollowed by addition of a solution
  3. stirringthe suspension was stirred at 0° C. for 1 hr
  4. filtrationThe solid was filtered
  5. washfirstly washed with 80 ml of de-ionized water
  6. customThen the solid was dried at 70° C.
  7. wait2000 Pa for 16 hr
  8. waitThe crude product (23.4 g) was taken up with 117 ml of tetrahydrofuran for 1 hr
  9. filtrationAfter filtration at 0° C. the crystallized product
  10. washwas washed with 25 ml of t-butylmethylether
  11. customwas then dried at 70° C.
  12. wait2000 Pa for 16 hr

Sources & evidence

ORD record
ord-642e080f79bf44dbb85a6996f1cc6a92
Source dataset
uspto-grants-2000_08
Patent number
US06103902

Reaction notes

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