5-(3-Nitro-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine → 5-(3-Amino-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine

HRID 2039533Notes

Reaction equation

HRID 2039533 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][C:8]1[N:17]2[N:18]=[C:19]([NH2:21])[N:20]=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1)([O-])=O>CN(C)C=O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:22]=[CH:23][CH:24]=1)[CH2:7][C:8]1[N:17]2[N:18]=[C:19]([NH2:21])[N:20]=[C:16]2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:9]=1

Participants

4

Reactant 1

HCID 670428025-(3-Nitro-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine

Product 1

HCID 699275525-(3-Amino-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamineYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(3-nitro-benzyl)-[1,2,4]triazolo[1,5-c]quinazolin-2-ylamine (0.10 g, 0.31 mmol), prepared as described in Example 2, in N,N-dimethylformamide (10 mL), 10% Pd/C (50% w/w, 0.05 g) was added. The mixture was reacted in Parr Apparatus at 40 p.s.i. for 5 h. The suspension was filtered through Celite®. After washing the filter with methanol, the solution was evaporated to dryness. The crude was twice crystallized from ethyl acetate to provide the title product (0.062 g, 67% yield).

Workup

  1. customThe mixture was reacted in Parr Apparatus at 40 p.s.i
  2. filtrationThe suspension was filtered through Celite®
  3. washAfter washing the
  4. filtrationfilter with methanol
  5. customthe solution was evaporated to dryness
  6. customThe crude was twice crystallized from ethyl acetate

Sources & evidence

ORD record
ord-749b572815d34ab989a5d2dd2c7e4ac1
Source dataset
uspto-grants-2013_11
Patent number
US08580783B2

Reaction notes

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