3-(1H-benzo[d]imidazol-2-yl)-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole → 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

HRID 1047528Notes

Reaction equation

HRID 1047528 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([N+:19]([O-])=O)[CH:17]=2)[N:12]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[N:11]=1.[H][H]>C(O)C.[Pd]>[NH:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[N:1]=[C:2]1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=2)[N:12]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[N:11]=1

Participants

5

Reactant 2

HCID 1363522443-(1H-benzo[d]imidazol-2-yl)-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amineYield 60%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(1H-Benzo[d]imidazol-2-yl)-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (50 mg, 0.137 mmol) was added to 10% Pd/C (10 mg) in ethanol (40 mL) and then pressurized with hydrogen (60 psi) for 6 h at room temperature. The reaction mixture was filtered through Celite, and the solvent was removed in vacuo. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound in 60% yield. 1H NMR (400 MHz, CD3OD): δ 7.69 (m, 2H), 7.55 (m, 2H), 7.26 (m, 2H), 7.05 (m, 1H), 5.84 (d, 1H, J=9.2 Hz), 4.00 (m, 1H), 3.82 (m, 1H), 2.65 (m, 1H), 2.14 (m, 2H), 1.78 (m, 3H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed in vacuo
  3. customPurification by flash chromatography (5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-55ef83365f6e4ae5be8ccac72ec66317
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

Loading…