Morpholine → 7-Bromo-3-(3-morpholin-4-yl-3-oxopropyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-one

HRID 2368595Notes

Reaction equation

HRID 2368595 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]3[C:12]([CH2:15][CH2:16][C:17](O)=[O:18])=[N:13][N:14]=[C:6]3[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:4]=2[N:3]=1.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl>[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]3[C:12]([CH2:15][CH2:16][C:17]([N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)=[O:18])=[N:13][N:14]=[C:6]3[N:5]([CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 250596563-(7-Bromo-5-oxo-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-3-yl)propanoic acid

Product 1

HCID 250599157-Bromo-3-(3-morpholin-4-yl-3-oxopropyl)-9-pentyl-6,9-dihydro-5h-[1,2,4]triazolo[4,3-a]purin-5-oneYield 63.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of 3-(7-bromo-5-oxo-9-pentyl-6,9-dihydro-5H[1,2,4]triazolo[4,3-a]purin-3-yl]propanoic acid (50 mg, 0.126 mmol), morpholine (21.0 mg, 0.252 mmol), triethylamine (25.5 mg, 0.252 mmol) and BOP (61.5 mg, 0.139 mmol) in CH2Cl2 (10 ml) was stirred at room temperature for 2 hours. After evaporation of solvent, the residue was purified by preparative LC-MS to afford the desired product (37.2 mg, 60%) as white solid. LCMS calculated for C18H25BrN7O3 (M+H): 466.1. Found: 466.1.

Workup

  1. customAfter evaporation of solvent
  2. customthe residue was purified by preparative LC-MS

Sources & evidence

ORD record
ord-9cc5eeb1ada847f9a9cdefb049687b97
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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