Cesium carbonate → HCID 87330182, compound

HRID 1040764Notes

Reaction equation

HRID 1040764 reaction equation
[CH:1]12[CH2:13][CH2:12][CH:8]([CH2:9][NH:10][CH2:11]1)[C:7]1[C:2]2=[CH:3][C:4]([NH2:14])=[CH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]#[N:24]>CC(C)=O>[NH2:14][C:4]1[CH:3]=[C:2]2[C:7](=[CH:6][CH:5]=1)[CH:8]1[CH2:12][CH2:13][CH:1]2[CH2:11][N:10]([CH2:22][C:23]#[N:24])[CH2:9]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 67263886HCID 67263886, compound

Product 1

HCID 87330182HCID 87330182, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10-Aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-4-ylamine (193 mg, 1.02 mmol) was dissolved in acetone (20 mL) and Cs2CO3 (994 mg, 3.06 mmol, 3.0 eq) and bromoacetonitrile (134 mg, 1.13 mmol, 91 μL, 1.1 eq) were added. The reaction was stirred at room temperature for 2 hours and was then concentrated under reduced pressure. The residue was taken up in CH2Cl2 (10 mL) and washed with water (10 mL). The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by silica gel chromatography using a gradient of 0-10% MeOH/CH2Cl2 as the eluting solvent to obtain (4-amino-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-acetonitrile as a brown oil (123 mg, 53%). LCMS (m/e) 227 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.87 (d, 1H, J=7.7 Hz), 6.50 (dd, 1H, J=2.4 and 7.7 Hz), 6.47 (d, 1H, J=2.3 Hz), 3.57 (bs, 2H), 3.52 (s, 2H), 3.00-2.90 (m, 2H), 2.99-2.80 (m, 2H), 2.61-2.50 (m, 2H), 2.20-2.05 (m, 2H), 1.70-1.63 (m, 2H).

Workup

  1. concentrationwas then concentrated under reduced pressure
  2. washwashed with water (10 mL)
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-4239ea58675241e2bf0089d76971303d
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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