3-Phenylpropylamine → HCID 86696333, compound

HRID 870639Notes

Reaction equation

HRID 870639 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8](Cl)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:12]1([CH2:18][CH2:19][CH2:20][NH2:21])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)CC>[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:21][CH2:20][CH2:19][CH2:18][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 162593-Phenylpropylamine2×HCID 128723233-Bromo-6-chloroimidazo(1,2-b)pyridazine

Product 1

HCID 86696333HCID 86696333, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-6-chloro-imidazo[1,2-b]pyridazine (232 mg, 1 mmol) and phenylpropyl amine (1 ml, 7 mmol) in n-PrOH (1 mL) was heated in a microwave at 150° C. for 20 min. Additional phenylpropyl amine (0.5 ml) was added and reaction mixture heated for additional 20 min. then 30 min. in a microwave. The reaction mixture was concentrated and the residue was subjected to ISCO (40 g column, DCM 3 min. then 0-10% MeOH in DCM over 30 min.) to gave the product (380 mg ˜90% pure and was used directly for next step).

Workup

  1. customreaction mixture
  2. temperatureheated for additional 20 min.
  3. custom30 min.
  4. concentrationThe reaction mixture was concentrated
  5. custom40 g column, DCM 3 min.
  6. custom0-10% MeOH in DCM over 30 min.) to gave the product (380 mg ˜90% pure

Sources & evidence

ORD record
ord-7cc1db67ef6e4b0980c19a8ac542c8ea
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

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