4-(2-(5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)morpholine → HCID 178507237, compound

HRID 1047560Notes

Reaction equation

HRID 1047560 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[N:8]=[C:7]2[C:19]1[NH:23][C:22]2[CH:24]=[C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:26]=[CH:27][C:21]=2[N:20]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[O:31]1[CH2:30][CH2:29][N:28]([C:25]2[CH:26]=[CH:27][C:21]3[NH:20][C:19]([C:7]4[C:6]5[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=5)[N:9]([CH:13]5[CH2:18][CH2:17][CH2:16][CH2:15][O:14]5)[N:8]=4)=[N:23][C:22]=3[CH:24]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 2

HCID 1363522614-(2-(5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 178507237HCID 178507237, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(2-(5-Nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imidazol-6-yl)morpholine (50 mg, 0.111 mmol) was added to the 10% Pd/C (10 mg) in ethanol (20 mL) and then hydrogen gas (60 psi) was applied for overnight at room temperature. Upon The reaction mixture was filtered through Celite, and the solvent was removed in vacuum. Purification by flash chromatography (5% CH3OH/CH2Cl2) afforded the title compound (25 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 7.66 (d, 1H, J=2.4 Hz), 7.56-7.51 (m, 2H), 7.15 (m, 1H), 7.06-7.01 (m, 2H), 5.81 (dd, 1H, J=2.4 and 9.6 Hz), 4.01 (m, 1H), 3.87 (m, 4H), 3.81 (m, 1H), 3.65 (t, 1H, J=6.8 Hz), 3.16 (m, 4H), 2.67-2.58 (m, 1H), 2.16 (m, 1H), 2.08 (m, 1H), 1.84 (m, 1H), 1.69 (m, 1H).

Workup

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

Sources & evidence

ORD record
ord-a495738879474b2f9e21fe0bf3cf7c0a
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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