HCID 89982657, compound → HCID 68294743, compound

HRID 1909344Notes

Reaction equation

HRID 1909344 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]([CH3:17])=[CH2:16])[CH:11]=[C:10]([C:18]([NH:20][CH2:21][C:22]4[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=4[CH3:28])=[O:19])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>[Pd]>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([CH:15]([CH3:16])[CH3:17])[CH:11]=[C:10]([C:18]([NH:20][CH2:21][C:22]4[C:23](=[O:30])[NH:24][C:25]([CH3:29])=[CH:26][C:27]=4[CH3:28])=[O:19])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 1

HCID 89982657HCID 89982657, compound

Product 1

HCID 68294743HCID 68294743, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1-Cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(prop-1-en-2-yl)-1H-indazole-4-carboxamide was reduced using the standard Pd—C hydrogenation conditions and purified by prep HPLC to afford the target compound as a TFA salt (35% yield). LCMS: 407.25 (M+1)+; HPLC: 97.79% (@ 254 nm) (Rt;7.285); 1H NMR (DMSO-d6, 400 MHz) δ 11.54 (s, 1H), 8.43 (t, 1H), 8.25 (s, 1H), 7.64 (s, 1H), 7.48 (s, 1H), 5.89 (s, 1H), 5.18 (m, 1H), 4.36 (d, 2H, J=4 Hz), 3.04 (m, 1H), 2.21 (s, 3H), 2.12 (s, 3H), 2.08 (m, 2H), 1.98 (m, 2H), 1.86 (m, 2H), 1.69 (m, 2H), 1.28 (d, 6H, J=6.8 Hz).

Workup

  1. custompurified by prep HPLC

Sources & evidence

ORD record
ord-0fb8e3a573f94800975c73fc444e2884
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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