3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester → HCID 178456576, compound

HRID 395287Notes

Reaction equation

HRID 395287 reaction equation
C[O:2][C:3](=[O:33])[CH2:4][CH2:5][C:6]12[CH2:13][CH2:12][C:9]([C:14]3[NH:22][C:21]4[C:20]([NH:23][CH:24]([CH2:27]O)[CH2:25][CH3:26])=[N:19][C:18](=[O:29])[N:17]([CH2:30][CH2:31][CH3:32])[C:16]=4[N:15]=3)([CH2:10][CH2:11]1)[CH2:8][CH2:7]2>O=S(Cl)Cl>[CH2:25]([CH:24]1[N:23]=[C:20]2[N:19]([C:18](=[O:29])[N:17]([CH2:30][CH2:31][CH3:32])[C:16]3[N:15]=[C:14]([C:9]45[CH2:12][CH2:13][C:6]([CH2:5][CH2:4][C:3]([OH:2])=[O:33])([CH2:7][CH2:8]4)[CH2:11][CH2:10]5)[NH:22][C:21]=32)[CH2:27]1)[CH3:26]

Participants

3

Reactant 1

HCID 691473133-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl]-propionic acid methyl ester

Product 1

HCID 178456576HCID 178456576, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

3-{4-[6-(1-Hydroxymethyl-propylamino)-2-oxo-3-propyl-3,7-dihydro-2H-purin-8-yl]-bicyclo[2.2.2]oct-1-yl}-propionic acid methyl ester (30 mg) was dissolved in 1 mL of SOCl2 and stirred under reflux for 15 min. The reaction mixture was then cooled to rt and concentrated under reduced pressure. The resulting residue was dissolved in a solution containing 1 mL of water, 0.5 mL of MeOH, and 0.1 mL of 10% aq. NaOH. The reaction mixture was stirred at rt for 30 min. It was then acidified to pH 2 with dilute 1 N HCl and concentrated. The resulting crude product was purified by preparative HPLC to afford the titled compound.

Workup

  1. temperatureunder reflux for 15 min
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in a solution
  4. additioncontaining 1 mL of water, 0.5 mL of MeOH, and 0.1 mL of 10% aq. NaOH
  5. stirringThe reaction mixture was stirred at rt for 30 min
  6. additionwith dilute 1 N HCl
  7. concentrationconcentrated
  8. customThe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-98208275fee94a90937a7d7596f79b36
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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