Hydrochloric Acid → HCID 11156453, compound

HRID 1871590Notes

Reaction equation

HRID 1871590 reaction equation
[Cl:1][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)[N:5]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:3]=1.[CH3:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([NH2:36])(=[O:35])=[O:34])=[N:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+].Cl>C1N2CCN(CC2)C1.O.CC(C)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([C:24]#[N:25])[CH:19]=2)[N:5]=[C:6]([NH:36][S:33]([C:30]2[CH:29]=[CH:28][C:27]([CH3:26])=[CH:32][N:31]=2)(=[O:35])=[O:34])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 36141995-Methyl-2-pyridinesulfonamideHCID 114629344-(4,6-Dichloro-5-(2-methoxyphenoxy)pyrimidin-2-yl)picolinonitrile

Product 1

HCID 11156453HCID 11156453, compoundYield 93.8%

Reagents, catalysts & solvents 3

HCID 9237DabcoCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

12.5 g (33.5 mmol) of 4-[4,6-dichloro-5-(2-methoxy-phenoxy)-pyrimidine-2-yl]-pyridine-2-carbonitrile and 6.06 g (35 mmol) of 5-methyl-pyridine-2-sulfonamide were added to 130 ml of acetone. 15 g of potassium carbonate and 190 mg (1.6 mmol) of 1,4-diazobicyclo[2.2.2]octane were added and the suspension was stirred at 40° C. for 5 hr and at 20° C. for 15 hr. Then 50 ml of de-ionized water were added followed by dropwise addition of 50 ml of 3 N hydrochloric acid (pH of the solution=1). Acetone was removed by evaporation and the suspension was stirred for 1 hr. The solid was filtered and washed with 100 ml of water. The residue was heated (reflux) in 100 ml of methanol for 1 hr followed by cooling to 20° C. The solid was filtered and dried at 80° C., 2000 Pa for 16 hr. There were obtained 16.0 g (93% of theory) of 5-methyl-pyridine-2-sulfonic acid [6-chloro-2-(2-cyano-pyridine-4-yl)-5-(2-methoxy-phenoxy)-pyrimidine-4-yl]-amide with a HPLC purity of 90.3% (w/w).

Workup

  1. customAcetone was removed by evaporation
  2. stirringthe suspension was stirred for 1 hr
  3. filtrationThe solid was filtered
  4. washwashed with 100 ml of water
  5. temperatureThe residue was heated
  6. temperature(reflux) in 100 ml of methanol for 1 hr
  7. temperatureby cooling to 20° C
  8. filtrationThe solid was filtered
  9. customdried at 80° C.
  10. wait2000 Pa for 16 hr

Sources & evidence

ORD record
ord-9f6584957668413db666871c736d9dba
Source dataset
uspto-grants-2000_08
Patent number
US06103902

Reaction notes

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