HCID 178418361, compound → HCID 178429874, compound

HRID 1047572Notes

Reaction equation

HRID 1047572 reaction equation
[CH3:1][CH:2]1[O:7][CH2:6][CH2:5][N:4]([C:8]2[CH:34]=[CH:33][C:11]3[NH:12][C:13]([C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[C:21]([N+:24]([O-])=O)[CH:22]=5)[N:17]([CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][O:28]5)[N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:3][N:4]([C:8]2[CH:34]=[CH:33][C:11]3[NH:12][C:13]([C:15]4[C:23]5[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=5)[N:17]([CH:27]5[CH2:32][CH2:31][CH2:30][CH2:29][O:28]5)[N:16]=4)=[N:14][C:10]=3[CH:9]=2)[CH2:5][CH2:6][O:7]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178429876HCID 178429876, compound

Product 1

HCID 178429874HCID 178429874, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Methyl-4-(2-(5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)-1H-benzo[d]imida-zol-5-yl)morpholine (60 mg, 0.130 mmol) was added to 10% Pd/C (10 mg) in ethanol (25 mL) and then hydrogen gas (60 psi) was applied for 8 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 (40 mg). 1H NMR: (400 MHz, CD3OD): δ 7.66 (d, 1H, J=2.0 Hz), 7.52 (m, 2H), 7.13 (s, 1H), 7.04-7.00 (m, 2H), 5.79 (dd, 1H, J=2.4 and 9.2 Hz), 3.97 (m, 2H), 3.79 (m, 3H), 3.49 (m, 1H), 3.41 (m, 1H), 2.76 (m, 1H), 2.62 (m, 1H), 2.44 (m, 1H), 2.13 (m, 1H), 2.05 (m, 1H), 1.80 (m, 1H), 1.68 (m, 2H), 1.22 (d, 3H, J=6.4 Hz); ESI-MS [M+H]+: 433.2.

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-1d08b49987d34363ad6075990900c83a
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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