Chloroacetaldehyde → HCID 21866982, compound

HRID 1766800Notes

Reaction equation

HRID 1766800 reaction equation
Cl[CH2:2][CH:3]=O.C([O:9][C:10](=[O:27])[C:11]1[C:16]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][C:19]=2[Cl:25])=[CH:15][C:14]([NH2:26])=[N:13][CH:12]=1)(C)(C)C>CCO.CCOC(C)=O>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:16]2[C:11]([C:10]([OH:9])=[O:27])=[CH:12][N:13]3[CH:2]=[CH:3][N:26]=[C:14]3[CH:15]=2)=[C:19]([Cl:25])[CH:20]=1

Participants

5

Reactant 2

HCID 33Chloroacetaldehyde2×HCID 68859908HCID 68859908, compound

Product 1

HCID 21866982HCID 21866982, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Chloroacetaldehyde (12 μL, 0.188 mmol) was added to a mixture of 6-amino-4-(4-bromo-2-chlorophenylamino)-nicotinic acid tert-butyl ester (42) (50 mg, 0.125 mmol) in EtOH (630 μL). After stirring the reaction mixture at 80° C. for 5 hours, an additional 12 μL of chloroacetaldehyde were added and heating was continued for 10 hours. The reaction mixture was cooled to room temperature and diluted with EtOAc to give a cloudy semi-solution. The organic layer was washed with water, saturated NaHCO3 and brine. The organic layer contains a precipitate, which was collected by filtration to give the desired product (43) (15 mg, 33%). MS APCI (−) m/z 364, 366, (M−, Cl, Br pattern) detected. 1H NMR (400 MHz, DMSO-d6) δ 9.12 (s, 1H), 8.31 (s, 1H), 7.91 (s, 1H), 7.80 (s, 1H), 7.65–7.54 (m, 2H), 6.91 (s, 1H).

Workup

  1. temperatureheating
  2. waitwas continued for 10 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. customto give a cloudy semi-solution
  5. washThe organic layer was washed with water, saturated NaHCO3 and brine
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-1d5dcca4e1b447ac9c6df8ac0069f89c
Source dataset
uspto-grants-2007_06
Patent number
US07230099B2

Reaction notes

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