Hydrochloric Acid → HCID 67318639, compound

HRID 2061040Notes

Reaction equation

HRID 2061040 reaction equation
[Br-].C(OC([NH:9][C:10]([C:13]1[N:14]=[N:15][N:16]([CH2:18][CH2:19][N+:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=1)([CH3:12])[CH3:11])=O)(C)(C)C.[ClH:24]>CO.O1CCOCC1>[ClH:24].[NH2:9][C:10]([C:13]1[N:14]=[N:15][N:16]([CH2:18][CH2:19][N+:20]([CH3:22])([CH3:21])[CH3:23])[CH:17]=1)([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67319904HCID 67319904, compound

Product 1

HCID 67318639HCID 67318639, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(4-(2-(tert-Butoxycarbonylamino)propan-2-yl)-1H-1,2,3-triazol-1-yl)-N,N,N-trimethylethanaminium bromide (6.20 g, 15.8 mmol) was dissolved in methanol (15 ml). To the solution was added 4M hydrogen chloride in dioxane (150 ml), and the combined reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was concentrated and dissolved in water. Silver oxide (6.0 g) was added to the aqueous solution and the mixture was stirred at room temperature for 30 minutes. The solution was filtered through Celite®, and concentrated hydrochloric acid (2 ml) was added to the solution. The solution was filtered through Celite® a second time, and the aqueous solution was concentrated in vacuo. The crude material was purified by prep-HPLC (5-95% gradient of water/methanol with 0.05% acetic acid) to give 3.29 g (84%) 2-(4-(2-aminopropan-2-yl)-1H-1,2,3-triazol-1-yl)-N,N,N-trimethylethanaminium hydrochloride. 1H NMR (D2O) δ 8.27 (s, 1H), 5.07 (t, J=5.0 Hz, 2 H), 4.03 (t, J=5.1 Hz, 2 H), 3.21 (s, 9 H), 1.78 (s, 6 H); MS (ESI+) calculated for C10H22N5+: 212.19. Found: 212.2 (M+).

Workup

  1. customthe combined reaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in water
  4. additionSilver oxide (6.0 g) was added to the aqueous solution
  5. stirringthe mixture was stirred at room temperature for 30 minutes
  6. filtrationThe solution was filtered through Celite®, and concentrated hydrochloric acid (2 ml)
  7. additionwas added to the solution
  8. filtrationThe solution was filtered through Celite® a second time
  9. concentrationthe aqueous solution was concentrated in vacuo
  10. customThe crude material was purified by prep-HPLC (5-95% gradient of water/methanol with 0.05% acetic acid)

Sources & evidence

ORD record
ord-d5664e5c09c74824a7f70f130219c780
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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