HCID 57758046, compound → Ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

HRID 2197518Notes

Reaction equation

HRID 2197518 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1>[Ni].C(O)C.C1COCC1>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][CH:21]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 1

HCID 57758046HCID 57758046, compound

Product 1

HCID 57758198Ethyl 4-amino-5-(4-aminophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylateYield 99.2%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Raney nickel was added to a flask containing ethanol (20 mL). The catalyst was triturated with ethanol (3×20 mL) and the a suspension of ethyl 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (4.0 g, 12.2 mmol) in ethanol (600 mL) and THF (200 mL) was added. The reaction was then placed under a hydrogen atmosphere (1 atm) and allowed to stir at rt overnight. The reaction was filtered through a pad of Celite® using a mixture of ethanol and THF (3:1) to rinse. The filtrate was concentrated in vacuo to afford the desired product (3.60 g, 96%). 1H-NMR (DMSO-d6) 8.05 (s, 1H), 8.04 (br s, 2H), 7.88 (s, 1H), 7.01 (d, J=8.0 Hz, 2H), 6.61 (d, J=8.0 Hz, 2H), 5.31 (br s, 2H), 4.07 (q, J=7.3 Hz, 2H), 1.12 (t, J=7.3 Hz, 3H); ES-MS m/z 298.2 (MH)+; HPLC RT (Method A) 1.64 min; TLC Rf=0.30 (Acetone/CH2Cl2 1:3).

Workup

  1. customThe catalyst was triturated with ethanol (3×20 mL)
  2. additionwas added
  3. filtrationThe reaction was filtered through a pad of Celite®
  4. additiona mixture of ethanol and THF (3:1)
  5. washto rinse
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d15664fb04aa4d55b91df3e548d434c2
Source dataset
uspto-grants-2012_12
Patent number
US08338594B2

Reaction notes

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