HCID 178418361, compound → HCID 178428192, compound

HRID 1047577Notes

Reaction equation

HRID 1047577 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([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)[CH2:4][CH2:3]1.[H][H]>C(O)C.[Pd]>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([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)[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178428194HCID 178428194, compound

Product 1

HCID 178428192HCID 178428192, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-(5-(4-Methylpiperidin-1-yl)-1H-benzo[d]imidazol-2-yl)-5-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (100 mg, 0.217 mmol) was added to 10% Pd/C (2.302 mg, 0.022 mmol) 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 (75 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 7.66 (d, 1H, J=2.0 Hz), 7.51 (m, 2H), 7.17 (bs, 1H), 7.05-7.00 (m, 2H), 5.78 (dd, 1H, J=2.4 & 9.2 Hz), 3.98 (m, 1H), 3.78 (m, 1H), 3.56 (m, 2H), 2.67 (m, 3H), 2.14-2.03 (m, 2H), 1.76 (m, 3H), 1.65 (m, 2H), 1.40 (m, 3H), 0.98 (d, 3H, J=6.0 Hz); ESI-MS [M+H]+: 431.3.

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-c730415ec2cf4bd9b5ed4253681823fb
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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