Water → HCID 17954015, compound

HRID 1432374Notes

Reaction equation

HRID 1432374 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][CH2:16][CH2:15]3)[N:3]=1.[H-].[Na+].[CH:23]1(Br)[CH2:27][CH2:26][CH2:25][CH2:24]1.O>CN(C=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[C:4]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[CH2:17][CH2:16][CH2:15]3)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178478380HCID 178478380, compound

Product 1

HCID 17954015HCID 17954015, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(2-Chloro-9H-purin-6-yl)-indan-5-yl-amine (857 mg, 3 mmol) was dissolved in dry DMF (10 mL). NaH (94 mg, 3.9 mmol) was added in portions and the resulting mixture was stirred for 1 h. Cyclopentyl bromide (760 mg, 5.1 mmol) was then added and the reaction was stirred overnight at 80° C. under N2. After cooling, H2O (50 mL) was added and the mixture was extracted with CH2Cl2 (3×25 mL). The combined extracts were washed with brine (2×25 mL), dried over MgSO4, and evaporated. The residue was purified by flash chromatography (95:5 CH2Cl2/Et2O) to afford the title compound as a white powder (738 mg, 69.5%). TLC (95:5 CH2Cl2/Et2O): RF=0.38.

Workup

  1. stirringthe reaction was stirred overnight at 80° C. under N2
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with CH2Cl2 (3×25 mL)
  4. washThe combined extracts were washed with brine (2×25 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (95:5 CH2Cl2/Et2O)

Sources & evidence

ORD record
ord-bfbf8dc9b55f4e81b67ba733f444cbf3
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

Loading…