1,3-Dichloroacetone → 2'-Amino-6'-[({2-[(3-chloro-4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]-6-(2-hydroxyethoxy)-3,4'-bipyridine-3',5'-dicarbonitrile

HRID 242169Notes

Reaction equation

HRID 242169 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH2:11])=[S:10])=[CH:4][C:3]=1[Cl:12].Cl[CH2:14][C:15]([CH2:17]Cl)=O.[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:29]=[N:30][C:31]([O:34][CH2:35][CH2:36][OH:37])=[CH:32][CH:33]=2)[C:23]([C:38]#[N:39])=[C:22]([SH:40])[N:21]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[NH2:19][C:20]1[C:25]([C:26]#[N:27])=[C:24]([C:28]2[CH:29]=[N:30][C:31]([O:34][CH2:35][CH2:36][OH:37])=[CH:32][CH:33]=2)[C:23]([C:38]#[N:39])=[C:22]([S:40][CH2:17][C:15]2[N:11]=[C:9]([NH:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[C:3]([Cl:12])[CH:4]=3)[S:10][CH:14]=2)[N:21]=1

Participants

6

Reactant 4

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 704698(3-Chloro-4-fluorophenyl)thioureaHCID 178510485HCID 178510485, compound

Product 1

HCID 247529062'-Amino-6'-[({2-[(3-chloro-4-fluorophenyl)amino]-1,3-thiazol-4-yl}methyl)thio]-6-(2-hydroxyethoxy)-3,4'-bipyridine-3',5'-dicarbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

209 mg (0.67 mmol) of 4-fluoro-3-chlorophenylthiourea and 89 mg (0.70 mmol) of 1,3-dichloroacetone are dissolved in 5 ml of DMF, and the reaction solution is stirred at 80° C. for 3 h. After cooling, 209 mg (0.67 mmol) of the compound from example 2A and 224 mg (2.67 mmol) of sodium bicarbonate are added, and the mixture is stirred at RT for a further 20 h. The mixture is then filtered through a paper filter, and sat. sodium bicarbonate solution (5 ml) is added to the filtrate. The aqueous phase is extracted with ethyl acetate (three times, 5 ml each). The combined organic phases are dried over sodium sulphate, and the solvent is removed on a rotary evaporator.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is stirred at RT for a further 20 h
  3. filtrationThe mixture is then filtered through a paper
  4. filtrationfilter
  5. additionsat. sodium bicarbonate solution (5 ml) is added to the filtrate
  6. extractionThe aqueous phase is extracted with ethyl acetate (three times, 5 ml each)
  7. dry with materialThe combined organic phases are dried over sodium sulphate
  8. customthe solvent is removed on a rotary evaporator

Sources & evidence

ORD record
ord-dab2dc9de9024257854fee9ff8b76989
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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