N,N-Dimethylaniline → HCID 57635942, compound

HRID 2109976Notes

Reaction equation

HRID 2109976 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13](O)[N:12]2[N:16]=[CH:17][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:36])=O>>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([Cl:36])[N:12]2[N:16]=[CH:17][C:18]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[N:24])=[C:11]2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178510968HCID 178510968, compound

Product 1

HCID 57635942HCID 57635942, compound

Procedure

A solution of compound (4) (6.0 g, 17.7 mmol) and N,N-dimethylaniline (2.24 mL, 17.7 mmol) in phosphorus oxychloride (20 mL) was heated to reflux in a sealed tube for 1 h. Solvent was removed and the residue was dissolved in EtOAc (200 mL) and washed with saturated aqueous NaHCO3, dilute HCl, followed by brine, dried over anhydrous Na2 SO4, filtered and concentrated to give 5-(2-benzylsulfanyl-4-chloro-pyrazolo[1,5-a][1,3,5]triazin-8-yl)-pentanenitrile (5), which was used directly for the next step.

Workup

  1. temperatureto reflux in a sealed tube for 1 h
  2. customSolvent was removed
  3. dissolutionthe residue was dissolved in EtOAc (200 mL)
  4. washwashed with saturated aqueous NaHCO3, dilute HCl
  5. customdried over anhydrous Na2 SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-494d485fe79f4cbba3b6128a1b3a07f5
Source dataset
uspto-grants-2009_04
Patent number
US07517882B2

Reaction notes

Loading…