Acetic Acid → HCID 86652368, compound

HRID 1625982Notes

Reaction equation

HRID 1625982 reaction equation
C(O)(=O)C.[CH:5]1([CH:8]=O)[CH2:7][CH2:6]1.[NH2:10][C:11]1[C:16]([NH2:17])=[CH:15][C:14]([Br:18])=[CH:13][N:12]=1.[BH4-].[Na+]>ClCCl>[Br:18][C:14]1[CH:15]=[C:16]([NH:17][CH2:8][CH:5]2[CH2:7][CH2:6]2)[C:11]([NH2:10])=[N:12][CH:13]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 123114CyclopropanecarboxaldehydeHCID 6911565-Bromopyridine-2,3-diamineHCID 4311764Sodium borohydride

Product 1

HCID 86652368HCID 86652368, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic acid (304 μl) and cyclopropanecarbaldehyde (406 μl) were added to a solution of 2,3-diamino-5-bromopyridine (1000 mg) in dichloromethane (25 ml) at room temperature, followed by stirring for 1 hour. Sodium tetrahydroborate (604 mg) was added to the reaction solution under ice-cooling, and the mixture was stirred with warming to room temperature for 22 hours. The reaction solution was extracted by adding a saturated aqueous sodium bicarbonate solution and dichloromethane. The resulting organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by flash column chromatography to give the title compound (286 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. extractionThe reaction solution was extracted
  4. additionby adding a saturated aqueous sodium bicarbonate solution and dichloromethane
  5. washThe resulting organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-500ef9f01ada4b1b98bbe9aab5186809
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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