Triethylamine → HCID 178522356, compound

HRID 2200103Notes

Reaction equation

HRID 2200103 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.CCN(CC)CC.[CH:16]1([C:19](Cl)=[O:20])[CH2:18][CH2:17]1>C(Cl)Cl>[OH:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:1][C:19]([CH:16]2[CH2:18][CH2:17]2)=[O:20])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 178507942HCID 178507942, compound

Product 1

HCID 178522356HCID 178522356, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 2-amino-pyridin-4-ol (5 g, 45.4 mmol) in DCM (30 mL), add Et3N (13.8 g, 136 mmol) and then cyclopropanecarbonyl chloride (14.2 g, 136 mmol) dropwise while keeping the temperature below 10° C. After addition, stir the reaction at room temperature for 16 hrs. Remove the solvent under reduced pressure, dissolve the residue in THF (40 mL), adjust pH=12 with 1N NaOH solution. Stir the mixture for 3 hrs. Concentrate to give the crude product. Purification by chromatography (silica gel, EtOAc:MeOH=9:1) affords the title compound (2.6 g, 32%).

Workup

  1. customthe temperature below 10° C
  2. additionAfter addition
  3. customthe reaction at room temperature for 16 hrs
  4. customRemove the solvent under reduced pressure
  5. dissolutiondissolve the residue in THF (40 mL)
  6. stirringStir the mixture for 3 hrs
  7. concentrationConcentrate
  8. customto give the crude product
  9. customPurification by chromatography (silica gel, EtOAc:MeOH=9:1)

Sources & evidence

ORD record
ord-3c3a8e2ce2144796b1c02ff3e011e5bf
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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