Triethylamine → HCID 56949208, compound

HRID 333060Notes

Reaction equation

HRID 333060 reaction equation
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.[CH3:33][C:34]1[CH:39]=[C:38]([NH:40][CH2:41][CH2:42][CH2:43]N)[CH:37]=[CH:36][N:35]=1.[O-2:45].[Al+3].[O-2].[O-2].[Al+3]>CN(C=O)C.C(#N)C>[CH3:33][C:34]1[CH:39]=[C:38]([NH:40][CH2:41][CH2:42][CH2:43][NH:16][C:11](=[O:45])/[CH:12]=[CH:13]/[CH2:14][CH2:15][CH3:10])[CH:37]=[CH:36][N:35]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 9989226AluminaHCID 66835428HCID 66835428, compound

Product 1

HCID 56949208HCID 56949208, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

(E)-4-Hex-2-enoic acid (23 mg, 0.2 mmol) and HBTU (76 mg, 0.2 mmol) were dissolved in a 1:1 mixture of anhydrous DMF and anhydrous acetonitrile (2 ml), after 5 minutes triethylamine (82 μl, 0.6 mmol) and N-(2-Methyl-4-pyridyl)propane-1,3-diamine hydrochloride (40 mg, 0.2 mmol) was added. To the mixture basic aluminium oxide was added, stirring was continued for one hour, the mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile) to yield 20.2 mg (0.077 mmol, 39%).

Workup

  1. additionwas added
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated to dryness under reduced pressure
  4. customThe residue was purified by preparative HPLC (gradient of water containing 0.1% NH3 and acetonitrile)
  5. customto yield 20.2 mg (0.077 mmol, 39%)

Sources & evidence

ORD record
ord-e5ccd4e16c13406981c436d0490597cd
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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