Acetonitrile → HCID 68866659, compound

HRID 1869224Notes

Reaction equation

HRID 1869224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[CH2:10][N:9]2[CH:17]([CH3:19])[CH3:18])=[CH:4][CH:3]=1.C(#N)C.C1([N:30]=[C:31]=[O:32])CCCCCC1.C(O)C(N)(CO)CO>C(Cl)CCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:11]3([CH2:16][CH2:15][N:14]([C:31]([NH2:30])=[O:32])[CH2:13][CH2:12]3)[CH2:10][N:9]2[CH:17]([CH3:19])[CH3:18])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6503Tris(hydroxymethyl)aminomethaneHCID 3356886Cycloheptyl isocyanateHCID 24899506HCID 24899506, compound

Product 1

HCID 68866659HCID 68866659, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

Treat 1-(4-Chlorophenyl)-2-isopropyl-2,7-diazaspiro[3.5]nonane, Isomer A (0.015 g) in ClCH2CH2Cl (1 mL) and acetonitrile (1 mL) with cycloheptyl isocyanate (18 uL), and the resulting mixture stirred at RT for 424 h. P—S Trisamine (Argoonaut, 4.64 mmol/g) (120 g) and ClCH2CH2Cl (2 mL) were added and the resulting mixture was shaken to 20 h. The reaction mixture was filtered, the resin washed with CH2Cl2 (2 mL). The resulting filtrate was concentrated in vacuo and then placed on a silica gel plate (1000 u) and eluted with CH2Cl2:MeOH (95:5) to give of 1-(4-chlorophenyl)-2-isopropyl-2,7-diazaspiro[3.5]nonane-7-carboxamide, white residue (0.0208 g). Add MeOH (0.5 mL) and 0.1N HCl in MeOH (1 mL), and concentrate in vacuo to give the title compound, as a white solid (0.0222 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe resin washed with CH2Cl2 (2 mL)
  3. concentrationThe resulting filtrate was concentrated in vacuo
  4. washeluted with CH2Cl2:MeOH (95:5)

Sources & evidence

ORD record
ord-1941e214b1f54504a708b8b3daac343c
Source dataset
uspto-grants-2009_12
Patent number
US07638526B2

Reaction notes

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