Hydrogen Bromide → Methyl [4-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-piperidin-1-ylpropyl)amino]methyl}phenyl]acetate hydrobromide

HRID 339943Notes

Reaction equation

HRID 339943 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:41])[N:6]2[CH2:16][CH2:17][CH2:18][N:19]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:32][CH:31]=1)[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[BrH:42]>CO>[BrH:42].[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[NH:4][C:5](=[O:41])[N:6]2[CH2:16][CH2:17][CH2:18][N:19]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([CH2:36][C:37]([O:39][CH3:40])=[O:38])=[CH:34][CH:35]=1)[CH2:20][CH2:21][CH2:22][N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67989365Methyl (4-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-piperidin-1-ylpropyl)amino]methyl}phenyl)acetate

Product 1

HCID 86705743Methyl [4-{[[3-(6-amino-2-butoxy-8-oxo-7,8-dihydro-9H-purin-9-yl)propyl](3-piperidin-1-ylpropyl)amino]methyl}phenyl]acetate hydrobromideYield 80.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The product of Example 1 (0.81 g, 1.42 mmol) in MeOH (30 g) was dissolved in MeOH (8 mL) and 48% aqueous HBr solution (0.16 mL, 1.4 mmol) added. The mixture was stirred at rt for 1 hr and concentrated in vacuo. MeOH (1.6 mL) and MTBE (6.4 mL) was added to residue and the suspension stirred at rt for 4 days. The suspension was filtered, the collected solid washed with MTBE (50 mL) and dried to give the title compound (734 mg); MS multimode (+) 568; 1H NMR (DMSO-d6): δ 9.86 (brs, 1H), 7.24 (d, 2H), 7.18 (d, 2H), 6.42 (br, 2H), 4.12 (t, 2H), 3.69 (t, 4H), 3.65 (s, 3H), 3.50 (s, 2H), 3.08-2.97 (m, 6H), 2.41 (m, 4H), 1.83-1.51 (m, 12H), 1.40-1.32 (m, 2H), 0.90 (t, 3H).

Workup

  1. concentrationconcentrated in vacuo
  2. additionMeOH (1.6 mL) and MTBE (6.4 mL) was added to residue
  3. stirringthe suspension stirred at rt for 4 days
  4. filtrationThe suspension was filtered
  5. washthe collected solid washed with MTBE (50 mL)
  6. customdried

Sources & evidence

ORD record
ord-e2373a5ad4cc4585983dc4cef22e5b07
Source dataset
uspto-grants-2014_11
Patent number
US08895570B2

Reaction notes

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