Acetic Acid → HCID 178489610, compound

HRID 1871592Notes

Reaction equation

HRID 1871592 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]#[N:15])[CH:9]=2)[N:5]=[C:4]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)(=[O:19])=[O:18])[C:3]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].O.[NH2:37][NH2:38].O.C(O)(=O)C>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([C:14]([NH:37][NH2:38])=[NH:15])[CH:9]=2)[N:5]=[C:4]([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)(=[O:19])=[O:18])[C:3]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 11156453N-(6-Chloro-2-(2-cyanopyridin-4-yl)-5-(2-methoxyphenoxy)pyrimidin-4-yl)-5-methylpyridine-2-sulfonamide

Product 1

HCID 178489610HCID 178489610, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

20 g (39 mmol) of 5-methyl-pyridine-2-sulfonic acid [6-chloro-2-(2-cyano-pyridine-4-yl)-5-(2-methoxy-phenoxy)-pyrimidine-4-yl]-amide were suspended in 100 ml of N,N-dimethyl formamide and 7.6 ml (156 mmol) of hydrazine hydrate were added within 15 min. The reaction mixture was allowed to warm up slowly to 20° C. After 17.5 hr, at a temperature of 15° C., 250 ml of de-ionized water were added followed by slow addition of 10.5 ml acetic acid (until pH=5.4). The resulting suspension was stirred for 2 hr at 20° C. and then for additional 2 hr 0° C. The solid was filtered off under suction, firstly washed with 200 ml of de-ionized water and thereafter with 100 ml of t-butylmethylether. The residue was dried at 40° C., 2000 Pa for 18 hr. There were obtained 21.7 g (102% of theory) of 5-methyl-pyridine-2-sulfonic acid [6-chloro-2-[2-(hydrazino-imino-methyl)-pyridine-4-yl]-5-(2-methoxy-phenoxy)-pyrimidine-4-yl]-amide with a HPLC purity of 81.4% (w/w).

Workup

  1. waitfor additional 2 hr 0° C
  2. filtrationThe solid was filtered off under suction
  3. washfirstly washed with 200 ml of de-ionized water
  4. customThe residue was dried at 40° C.
  5. wait2000 Pa for 18 hr

Sources & evidence

ORD record
ord-0a25713bb0dd40f59ab7e4f12a609124
Source dataset
uspto-grants-2000_08
Patent number
US06103902

Reaction notes

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