Hydrochloric Acid → HCID 117697852, compound

HRID 1778515Notes

Reaction equation

HRID 1778515 reaction equation
[OH:1][N:2]=[C:3]1[CH2:10][CH:9]2[N:11](C(OC(C)(C)C)=O)[CH:5]([CH2:6][O:7][CH2:8]2)[CH2:4]1.[Li][CH2:20]CCC.CN(C=O)C.Cl>C1COCC1>[CH:9]12[NH:11][CH:5]([CH2:6][O:7][CH2:8]1)[CH2:4][C:3]1[C:10]2=[CH:20][O:1][N:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 117697857HCID 117697857, compoundHCID 178418339Butyllithium

Product 1

HCID 117697852HCID 117697852, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of compound 104b (512 mg, 2 mmol, 1.0 eq) in THF (10 mL) was added n-BuLi (5 mL, 2.0 M, 5.0 eq) dropwise at −50° C. After 30 min, dry DMF (740 mg, 10 mmol, 5.0 eq) in THF (2 mL) was added dropwise, the mixture was stirred for another 2 h from −60° C. to room temperature. To it 12 N HCl (1 mL) was added and refluxed for 2 h. The reaction mixture was concentrated to give 4,10-Dioxa-5,12-diaza-tricyclo[6.3.1.0*2,6*]dodeca-2,5-diene 104a (332 mg) as an oil. MS: calc'd (MH+) 167, measured (MH+) 167.

Workup

  1. temperaturerefluxed for 2 h
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-0cd5a0c816d9449283b09ec485663938
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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