N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amine → Hydrochloric Acid

HRID 1519135Notes

Reaction equation

HRID 1519135 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[N:12](CC2C=CC=CC=2)[N:13]=[N:14][CH:15]=1.[H][H]>CO.CCOC(C)=O.[Pd].Br[Zn]Br>[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[NH:10][C:11]1[CH:15]=[N:14][NH:13][N:12]=1.[ClH:9]

Participants

8

Reactant 2

HCID 86724056N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amineHCID 178418361HCID 178418361, compound

Product 2

HCID 313Hydrochloric AcidHCID 75203051N-(2-(Aminomethyl)-4-chlorophenyl)-2H-1,2,3-triazol-4-amine

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 24375Zinc bromide (ZnBr2); Zinc DibromideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-[2-(aminomethyl)-4-chloro-phenyl]-3-benzyl-triazol-4-amine 7b (439 mg, 1.40 mmol) in dry MeOH (18 mL) and EtOAc (18 mL) was treated with dibromozinc (126.0 mg, 0.56 mmol). The degassed mixture was then treated with 10% palladium on carbon (297.8 mg, 0.28 mmol) before affixing a hydrogen balloon. The mixture was stirred at room temperature for 2 h before filtering through celite and concentrating. The material was purified on an ISCO (0-100% MeOH in DCM) and the freebase was stirred in 4N HCl in dioxane for 30 min before evaporating to afford the title compound I-34 (mono hydrochloride salt) as a solid (291 mg, 80%). 1H NMR (500 MHz, DMSO-d6) δ 8.52 (1H, s) 8.47 (3H, m), 7.63 (1H, d), 7.53 (s, 1H), 7.48 (1H, d), 7.31 (1H, d) 4.12 (2H, q). MS m/z: 224.1 (M+H)+.

Workup

  1. filtrationbefore filtering through celite
  2. concentrationconcentrating
  3. customThe material was purified on an ISCO (0-100% MeOH in DCM)
  4. stirringthe freebase was stirred in 4N HCl in dioxane for 30 min
  5. custombefore evaporating

Sources & evidence

ORD record
ord-edc56fd371044f14806834a9e4386899
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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