Cyclopropylamine → HCID 178482046, compound

HRID 922458Notes

Reaction equation

HRID 922458 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=O)=[CH:2]1.[CH:12]1([NH2:15])[CH2:14][CH2:13]1>C(O)C>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3](/[CH:10]=[N:15]/[CH:12]2[CH2:14][CH2:13]2)=[CH:2]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Product 1

HCID 178482046HCID 178482046, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde (1.46 g) in ethanol (30 mL) was added cyclopropylamine (1.41 mL), and the mixture was stirred at 50° C. for 19 hours. The reaction solution was concentrated under reduced pressure, and then treated azeotropically with toluene. The resulting residue was triturated with isopropyl ether/n-hexane (3:1) to give N-[(1E)-1H-Pyrrolo[2,3-b]pyridin-3-ylmethylene]cyclopropylamine [REx(28-1)] (1.75 g) as a colorless powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiontreated azeotropically with toluene
  3. customThe resulting residue was triturated with isopropyl ether/n-hexane (3:1)

Sources & evidence

ORD record
ord-55d8d7d137fd4433a6405983a73e1342
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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