Stannous chloride dihydrate → HCID 68277229, compound

HRID 1048772Notes

Reaction equation

HRID 1048772 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[C:7]([C:21]#[N:22])=[N:8][C:9]([NH:12][C:13]2[CH:18]=[C:17]([F:19])[CH:16]=[C:15]([F:20])[CH:14]=2)=[CH:10][CH:11]=1.O.O.Cl[Sn]Cl>O.Cl>[F:19][C:17]1[CH:18]=[C:13]([NH:12][C:9]2[N:8]=[C:7]3[C:21]([NH2:1])=[N:22][NH:5][C:6]3=[CH:11][CH:10]=2)[CH:14]=[C:15]([F:20])[CH:16]=1

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 23668193Sodium NitriteHCID 68276600HCID 68276600, compound

Product 1

HCID 68277229HCID 68277229, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 713 mg of NaNO2 (10.3 mmol) in water (5 ml) is added, drop by drop, to a stirring solution of 2.3 g of 3-amino-6-(3,5-difluorophenylamino)picolinonitrile (9.4 mmol) in 100 ml of 6 N hydrochloric acid at 0° C. The mixture is stirred for 20 minutes at 0-5° C. A solution of 5.3 g of SnCl2.2H2O (23.5 mmol, 2.5 eq) in hydrochloric acid (12 N solution, 30 ml) is then added drop by drop and the solution is stirred for 1 hour at room temperature. The reaction medium is then cooled at 0° C. and basified to pH 8 using 30% soda solution. The mixture is extracted with ethyl acetate and washed using saturated NaCl solution and the organic phase is dried on anhydrous sodium sulfate before being concentrated under vacuum. The residue is purified by silica column chromatography (AcOEt). A light yellow solid is obtained (530 mg, 22%).

Workup

  1. customat 0° C
  2. stirringthe solution is stirred for 1 hour at room temperature
  3. temperatureThe reaction medium is then cooled at 0° C. and basified to pH 8
  4. extractionThe mixture is extracted with ethyl acetate
  5. washwashed
  6. dry with materialthe organic phase is dried on anhydrous sodium sulfate
  7. concentrationbefore being concentrated under vacuum
  8. customThe residue is purified by silica column chromatography (AcOEt)
  9. customA light yellow solid is obtained (530 mg, 22%)

Sources & evidence

ORD record
ord-f74064f41c754dd8a303a4cb9e90dfad
Source dataset
uspto-grants-2016_07
Patent number
US09381195B2

Reaction notes

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