Water → 2-(8-(3-Aminoazepan-1-yl)-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

HRID 984833

Reaction equation

HRID 984833 reaction equation
Br[C:2]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=2[C:14]#[N:15])[C:9]2[C:8](=[O:20])[NH:7][C:6](=[O:21])[N:5]([CH3:22])[C:4]=2[N:3]=1.[NH:23]1[CH2:29][CH2:28][CH2:27][CH2:26][CH:25]([NH2:30])[CH2:24]1.C(N(CC)CC)C.O>CS(C)=O.ClCCl>[NH2:30][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][N:23]([C:2]2[N:10]([CH2:11][C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[C:14]#[N:15])[C:9]3[C:8](=[O:20])[NH:7][C:6](=[O:21])[N:5]([CH3:22])[C:4]=3[N:3]=2)[CH2:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2756445Azepan-3-amineHCID 225085992-(8-Bromo-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

Product 1

HCID 225086232-(8-(3-Aminoazepan-1-yl)-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

2-(8-Bromo-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropurin-7-ylmethyl)benzonitrile (79A) (181 mg, 0,5 mmol) and azepan-3-ylamine (342 mg, 3 mmol), and triethylamine (0.35 ml, 2.5 mmol) were dissolved in 20 ml of DMSO and the mixture was subjected to microwaves (method F, 100° C., 300 W) for four hours. To the reaction mixture was added 100 ml of water and 100 ml of dichloromethane, and the organic layer was separated and dried over sodium sulfate. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=6.22 min.). Evaporation of the solvent afforded the title compound as an yellow oil.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. customThe solvents were evaporated
  4. customthe crude product was purified by preparative HPLC (method A1, Rt=6.22 min.)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-c35c071fc27a44d4bfdd3cd323d8e0a8
Source dataset
uspto-grants-2005_03
Patent number
US06869947B2

Linked notes

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