Tetrahydrofuran → HCID 59543423, compound

HRID 1798955Notes

Reaction equation

HRID 1798955 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([CH2:11][C:12]3[N:17]=[CH:16][C:15]([C:18]4[CH:25]=[CH:24][C:21]([C:22]#N)=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.C1C[O:38]CC1>C(Cl)Cl>[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([CH2:11][C:12]3[N:17]=[CH:16][C:15]([C:18]4[CH:25]=[CH:24][C:21]([CH:22]=[O:38])=[CH:20][CH:19]=4)=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 59543425HCID 59543425, compound

Product 1

HCID 59543423HCID 59543423, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-[6-(4-Cyclobutylpiperazin-1-ylmethyl)pyridin-3-yl]benzonitrile (0.066 g, 0.2 mmol) was dissolved in DCM (1 mL) DIBAL 1M in THF (0.2 mL) was added. The reaction mixture was stirred at RT for 1 hour. LC-MS showed no product. Another 1.5 eq. of DIBAL (0.2 mL) was added and stirring continued 1 hour. LC-MS showed full conversion. The reaction mixture was stored at −20° C. for 3 days. The reaction mixture was added DCM (5 mL) and cold NH4Claq (5 mL). The DCM phase was washed with water (5 mL) and brine (5 mL), dried with MgSO4, filtered and evaporation afforded the title compound as the free base. 34.5 mg (51%).

Workup

  1. additionwas added
  2. stirringstirring continued 1 hour
  3. waitThe reaction mixture was stored at −20° C. for 3 days
  4. washThe DCM phase was washed with water (5 mL) and brine (5 mL)
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customevaporation

Sources & evidence

ORD record
ord-bf4011fba60641f182468c08d6d6dc7f
Source dataset
uspto-grants-2013_01
Patent number
US08344001B2

Reaction notes

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