Tyramine → Lhd-221

HRID 1422473Notes

Reaction equation

HRID 1422473 reaction equation
[S:1]1[CH:5]=[C:4]([C:6]2[N:14]=[C:13]3[C:9]([N:10]=[CH:11][N:12]3[CH:15]([CH3:17])[CH3:16])=[C:8](Cl)[N:7]=2)[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.[NH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1>CC(O)C>[S:1]1[CH:5]=[C:4]([C:6]2[N:14]=[C:13]3[C:9]([N:10]=[CH:11][N:12]3[CH:15]([CH3:17])[CH3:16])=[C:8]([NH:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)[N:7]=2)[C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2

Participants

4

Reactant 2

HCID 5610Tyramine2×HCID 594089202-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine

Product 1

HCID 46199207Lhd-221

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

2-(benzo[b]thiophen-3-yl)-6-chloro-9-isopropyl-9H-purine (2.2 g, 0.0067 mol) was suspended in anhydrous 2-propanol (70 mL) in a pressure tube. Tyramine (1.01 g, 0.0074 mol) was added. The tube was sealed and heated at 85° C. for 16 hr. Additional tyramine (0.50 g, 0.0037 mol) was added and the mixture was heated at 85° C. for 48 hr. The reaction was concentrated. Aqueous sodium bicarbonate solution was added to the residue, which was extracted with EtOAc. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by column chromatography on silica gel, eluting with 50 to 85% EtOAc in hexane to afford a solid. The solid was triturated with methanol to provide the title compound as an off-white solid.

Workup

  1. customThe tube was sealed
  2. temperaturethe mixture was heated at 85° C. for 48 hr
  3. concentrationThe reaction was concentrated
  4. additionAqueous sodium bicarbonate solution was added to the residue, which
  5. extractionwas extracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with 50 to 85% EtOAc in hexane
  11. customto afford a solid
  12. customThe solid was triturated with methanol

Sources & evidence

ORD record
ord-4f0d287877504aa18615d2d8e365560c
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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