Chloroacetaldehyde → HCID 21866997, compound

HRID 917026Notes

Reaction equation

HRID 917026 reaction equation
Cl[CH2:2][CH:3]=O.C([O:9][C:10](=[O:28])[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])=[C:15]([F:26])[C:14]([NH2:27])=[N:13][CH:12]=1)(C)(C)C>CCO>[Br:24][C:21]1[CH:22]=[CH:23][C:18]([NH:17][C:16]2[C:11]([C:10]([OH:9])=[O:28])=[CH:12][N:13]3[CH:2]=[CH:3][N:27]=[C:14]3[C:15]=2[F:26])=[C:19]([Cl:25])[CH:20]=1

Participants

4

Reactant 2

HCID 33Chloroacetaldehyde2×HCID 68860780HCID 68860780, compound

Product 1

HCID 21866997HCID 21866997, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Chloroacetaldehyde (23 μL, 0.360 mmol) was added to a mixture of 6-amino-4-(4-bromo-2-chlorophenylamino)-5-fluoronicotinic acid tert-butyl ester (45) (75 mg, 0.180 mmol) in EtOH (1 mL). After stirring the reaction mixture at 70° C. for 10 hours, an additional 10 μL chloro-acetaldehyde was added and heating was continued for 33 hours. The reaction mixture was cooled to room temperature and desired product (46) was collected by filtration. The filtrate was diluted with EtOAc and washed with water, saturated NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated to give additional product (46) (51 mg, 74% combined recovery).

Workup

  1. temperatureheating
  2. waitwas continued for 33 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationdesired product (46) was collected by filtration
  5. additionThe filtrate was diluted with EtOAc
  6. washwashed with water, saturated NaHCO3 and brine
  7. dry with materialThe organic layer was dried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-34b7caf58887402c950f188c0401358d
Source dataset
uspto-grants-2007_09
Patent number
US07271178B2

Reaction notes

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