HCID 66551444, compound → HCID 66551246, compound

HRID 1909317Notes

Reaction equation

HRID 1909317 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[CH2:16][C:17]([CH3:24])([CH3:23])[NH:18][C:19]([CH3:22])([CH3:21])[CH:20]=4)[CH:11]=[C:10]([C:25]([NH:27][CH2:28][C:29]4[C:30](=[O:37])[NH:31][C:32]([CH3:36])=[CH:33][C:34]=4[CH3:35])=[O:26])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]4[CH2:16][C:17]([CH3:23])([CH3:24])[NH:18][C:19]([CH3:22])([CH3:21])[CH2:20]4)[CH:11]=[C:10]([C:25]([NH:27][CH2:28][C:29]4[C:30](=[O:37])[NH:31][C:32]([CH3:36])=[CH:33][C:34]=4[CH3:35])=[O:26])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 66551444HCID 66551444, compound

Product 1

HCID 66551246HCID 66551246, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

To a stirred solution of 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(2,2,6,6-tetramethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indazole-4-carboxamide (0.15 g, 0.29 mmol) in MeOH (2 mL), 10% Pd/C in catalytic amount was added and stirred it at room temperature under a hydrogen balloon for 3 hr. On completion of reaction, reaction mixture was filtered through a celite bed and the filtrate concentrated under reduced pressure to give 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(2,2,6,6-tetramethylpiperidin-4-yl)-1H-indazole-4-carboxamide (0.09, 66.4%). LCMS: 504.25 (M+1)+; HPLC: 99.77% (@ 254 nm) (Rt;5.460); 1H NMR (DMSO-d6, 400 MHz) δ 11.55 (bs, 1H), 8.43 (t, 1H, J=5.2 Hz), 8.26 (s, 1H), 7.70 (s, 1H), 7.50 (s, 1H), 5.89 (s, 1H), 5.22-5.18 (m, 1H), 4.36 (d, 2H, J=5.2 Hz), 3.33 (1H merged with DMSO peak), 2.22 (s, 3H), 2.12 (s, 3H), 2.09 (m, 2H), 1.99-1.87 (m, 4H), 1.73-1.66 (m, 4H), 1.52 (m, 2H), 1.32 (s, 6H), 1.18 (s, 6H).

Workup

  1. customOn completion of reaction, reaction mixture
  2. filtrationwas filtered through a celite bed
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-1f4fb280137a4c1f91b03c59488ac4b1
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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