HCID 118075733, compound → HCID 118086524, compound

HRID 1051723Notes

Reaction equation

HRID 1051723 reaction equation
[CH:1]1([C:4]([N:6]2[C:15]3[C:10](=[C:11]([O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:12]([N:16]4[CH:20]=[C:19]([C:21]5[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=5)[CH:18]=[N:17]4)=[CH:13][CH:14]=3)[CH2:9][CH2:8][C@@H:7]2[CH3:41])=[O:5])[CH2:3][CH2:2]1>[Pd].CO>[CH:1]1([C:4]([N:6]2[C:15]3[C:10](=[C:11]([O:34][C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:12]([N:16]4[CH:20]=[C:19]([CH:21]5[CH2:22][CH2:23][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:25][CH2:26]5)[CH:18]=[N:17]4)=[CH:13][CH:14]=3)[CH2:9][CH2:8][C@@H:7]2[CH3:41])=[O:5])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 118075733HCID 118075733, compound

Product 1

HCID 118086524HCID 118086524, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (5)-tert-butyl 4-(1-(1-(cyclopropanecarbonyl)-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinolin-6-yl)-1H-pyrazol-4-yl)-5,6-dihydropyridine-1(2H)-carboxylate (0.050 g, 0.09 mmol) and palladium on charcoal (10% wt %, 0.040 g) in methanol (15 mL) stirred under an atmosphere of hydrogen for 20 min at room temperature. The reaction mixture was filtered and concentrated under vacuum to afford (S)-tert-butyl 4-(1-(1-(cyclopropanecarbonyl)-2-methyl-5-phenoxy-1,2,3,4-tetrahydroquinolin-6-yl)-1H-pyrazol-4-yl)piperidine-1-carboxylate (0.048 g, 99%) as a white solid. MS (ESI, pos. ion) m/z 557 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c73212e1e874373b91dca9f5e3a82a7
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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