Triethylamine → HCID 121393717, compound

HRID 1480026Notes

Reaction equation

HRID 1480026 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[C:5](=[O:17])[NH:4][C:3]=1[C:18]1[N:22]([C:23]2[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=2)[N:21]=[CH:20][CH:19]=1.[CH2:31]([N:33]([CH2:36]C)[CH2:34]C)[CH3:32].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=[O:40].CNCC>C(Cl)Cl.CCOC(C)=O.C1CCCCC1>[C:27]([C:26]1[CH:25]=[CH:24][C:23]([N:22]2[C:18]([C:3]3[N:4]([C:34]([N:33]([CH2:31][CH3:32])[CH3:36])=[O:40])[C:5](=[O:17])[N:6]([C:7]4[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=4)[C:2]=3[CH3:1])=[CH:19][CH:20]=[N:21]2)=[CH:30][CH:29]=1)#[N:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 12219N-MethylethylamineHCID 821294-Nitrophenyl chloroformateHCID 121393736HCID 121393736, compound

Product 1

HCID 121393717HCID 121393717, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent3×HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(5-{5-Methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1H-imidazol-4-yl}-1H-pyrazol-1-yl)benzonitrile (Example 1) (107 mg, 0.262 mmol) was stirred in DCM (3 mL) and triethylamine (0.109 mL, 0.786 mmol) with N,N-dimethylaminopyridine (2 mg). To this mixture was added 4-nitrophenyl chloroformate (106 mg, 0.524 mmol) and the resulting mixture stirred at RT for 1 h. N-methylethylamine (93 mg, 1.57 mmol) in DCM (1 mL) was then added and stirring was continued for a further 2 h. The mixture was diluted with more DCM, washed with water, the organic phase separated, dried over Na2SO4 and evaporated. The product was purified by chromatography on a 12 g silica gel column, eluting with a gradient of 20% to 60% EtOAc in cyclohexane. The gum thus obtained was dissolved in a small quantity (<1 mL) of EtOAc and diluted with cyclohexane resulting in a formation of a white solid which was filtered off and dried. (65 mg, 50%).

Workup

  1. stirringstirring
  2. waitwas continued for a further 2 h
  3. washwashed with water
  4. customthe organic phase separated
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe product was purified by chromatography on a 12 g silica gel column
  8. washeluting with a gradient of 20% to 60% EtOAc in cyclohexane
  9. customThe gum thus obtained
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-146c708fdeed4b44978890fe7ec05b25
Source dataset
uspto-grants-2016_08
Patent number
US09409870B2

Reaction notes

Loading…