Triethylamine → HCID 67001723, compound

HRID 559484Notes

Reaction equation

HRID 559484 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[NH2:34][C:35]1[CH:44]=[CH:43][CH:42]=[C:41]2[C:36]=1[CH:37]=[CH:38][N:39]=[CH:40]2.C([N:47]([CH2:50]C)CC)C>C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:47][C:50]([NH:34][C:35]2[CH:44]=[CH:43][CH:42]=[C:41]3[C:36]=2[CH:37]=[CH:38][N:39]=[CH:40]3)=[O:24])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 707665-AminoisoquinolineHCID 199401P,P-Diphenylphosphinic azideHCID 27356471-((Tert-butoxy)carbonyl)piperidine-3-carboxylic acid

Product 1

HCID 67001723HCID 67001723, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 1-(tert-butoxycarbonyl)-3-piperidine carboxylic acid (1 g, 4.4 mmol) in toluene (10 ml) and triethylamine (0.68 ml) was added diphenylphosphoryl azide (1.1 eq., 1.33 g). Reaction was heated at reflux for 1 h and cooled. 5-Aminoisoquinoline (629 mg, 4.4 mmol) was added and reaction stirred at ambient temperature for 56 h. Solvent was removed under reduced pressure and the residue chromatographed on silica gel eluting with hexane/ethyl acetate (gradient elution, maximum 50%) to affored the title compound as a foam.

Workup

  1. customReaction
  2. temperaturewas heated
  3. temperatureat reflux for 1 h
  4. temperaturecooled
  5. customreaction
  6. customSolvent was removed under reduced pressure
  7. customthe residue chromatographed on silica gel eluting with hexane/ethyl acetate (gradient elution, maximum 50%) to affored the title compound as a foam

Sources & evidence

ORD record
ord-1cc0ba5f3101446e9dd01e0d799cad48
Source dataset
uspto-grants-2011_11
Patent number
US08063078B2

Reaction notes

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