HCID 89649393, compound → HCID 89660279, compound

HRID 2274592Notes

Reaction equation

HRID 2274592 reaction equation
[CH2:1]([N:5]([CH2:44][CH2:45][CH2:46][CH3:47])[C:6]([C:8]1[CH:12]=[C:11]([CH3:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[C:23]([N:25]2[C@H:34]([CH2:35][O:36][Si:37]([C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:39])[CH3:38])[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[N:9]=1)=[O:7])[CH2:2][CH2:3][CH3:4]>CCO.[Pd]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([N:10]2[C:11]([CH3:13])=[CH:12][C:8]([C:6]([N:5]([CH2:44][CH2:45][CH2:46][CH3:47])[CH2:1][CH2:2][CH2:3][CH3:4])=[O:7])=[N:9]2)=[C:15]([C:23]([N:25]2[C@H:34]([CH2:35][O:36][Si:37]([C:40]([CH3:42])([CH3:41])[CH3:43])([CH3:39])[CH3:38])[CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[CH:16]=1

Participants

4

Reactant 1

HCID 89649393HCID 89649393, compound

Product 1

HCID 89660279HCID 89660279, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)—N,N-dibutyl-1-(2-(3-(((tert-butyldimethylsilyl)-oxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-nitrophenyl)-5-methyl-1H-pyrazole-3-carboxamide (3.0 g, 4.5 mmol) in EtOH (50 mL) was added 10% Pd—C(0.3 g) followed by stirring under H2 balloon pressure at RT for 3 h. The reaction mixture was filtered through celite, the bed was washed with EtOH (150 mL) and the filtrate was concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford the title compound as an ‘off white’ solid 2.0 g (69%). Rf=0.45 (25% EtOAc in hexane); 1H NMR (400 MHz, DMSO-d6): δ 7.40-6.82 (m, 5H), 6.80-6.20 (m, 3H), 5.74-5.50 (m, 2H), 5.10-4.00 (m, 2H), 3.99-2.20 (m, 9H), 2.20-2.00 (m, 3H), 1.60-0.58 (m, 23H), 0.00-−0.04 (m, 6H); LC-MS: m/z 632.6 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe bed was washed with EtOH (150 mL)
  3. concentrationthe filtrate was concentrated invacuo
  4. customThe residue was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-da05b7398aba485b8536f870b8558112
Source dataset
uspto-grants-2015_09
Patent number
US09126979B2

Reaction notes

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