Triethylamine → HCID 178487291, compound

HRID 538079Notes

Reaction equation

HRID 538079 reaction equation
C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:32][O:33][C:34]1[CH:35]=[CH:36][C:37]2[N:41]([CH3:42])[C:40](=[O:43])[N:39]([CH2:44][C@H:45]3[CH2:50][CH2:49][C@H:48]([C:51]([OH:53])=O)[CH2:47][CH2:46]3)[C:38]=2[CH:54]=1.[C:55]([O:59][C:60]([N:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1)=[O:61])([CH3:58])([CH3:57])[CH3:56]>CN(C=O)C>[C:55]([O:59][C:60]([N:62]1[CH2:67][CH2:66][N:65]([C:51]([C@H:48]2[CH2:47][CH2:46][C@H:45]([CH2:44][N:39]3[C:38]4[CH:54]=[C:34]([O:33][CH3:32])[CH:35]=[CH:36][C:37]=4[N:41]([CH3:42])[C:40]3=[O:43])[CH2:50][CH2:49]2)=[O:53])[CH2:64][CH2:63]1)=[O:61])([CH3:58])([CH3:56])[CH3:57]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178487293HCID 178487293, compound

Product 1

HCID 178487291HCID 178487291, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethyl amine (0.39 ml, 2.77 mmol) was added to solution of HATU (1.05 g, 2.77 mmol) and trans-4-(6-Methoxy-3-methyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarboxylic acid (0.8 g, 2.5 mmol) in DMF (15 ml). The mixture was stirred at room temperature for 20 minutes and then tert-butyl-1-piperazinecarboxylate (0.47 g, 2.52 mmol) was added. The mixture was stirred at room temperature overnight, the solvent was removed under reduced pressure and the crude product was dissolved in DCM (50 ml). The organic solution was washed with HCl 1M (2×40 ml) and then with a saturated solution of NaHCO3. The organic solution was dried over Na2SO4, filtered and the solvent removed. Purification by silica column using cyclohexane/EtOAc (8/1) as eluent gave the titled compound (960 mg, 78%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe crude product was dissolved in DCM (50 ml)
  4. washThe organic solution was washed with HCl 1M (2×40 ml)
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed
  8. customPurification by silica column

Sources & evidence

ORD record
ord-25d83281913a45d391754aef2d1c7d4e
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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