HCID 89660113, compound → HCID 89649918, compound

HRID 2274567Notes

Reaction equation

HRID 2274567 reaction equation
[CH2:1]([N:5]([CH2:37][CH2:38][CH2:39][CH3:40])[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][OH:36])[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]([CH2:37][CH2:38][CH2:39][CH3:40])[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][OH:36])[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 89660113HCID 89660113, compound

Product 1

HCID 89649918HCID 89649918, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of (S)—N,N-dibutyl-1-(2-(3-(hydroxymethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-nitrophenyl)-5-methyl-1H-pyrazole-3-carboxamide (1.1 g, 2.0 mmol) in EtOH (10 mL) was added 10% Pd—C (0.04 g) followed by stirring under H2 balloon pressure at RT for 5 h. The reaction mixture was filtered through celite, the bed was washed with EtOH (20 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 0.8 g (77%). Rf=0.33 (40% EtOAc in hexane); 1H NMR (400 MHz, DMSO-d6): δ 7.30-6.82 (m, 5H), 6.80-6.15 (m, 3H), 5.72-5.50 (m, 2H, D2O exchangeable), 5.20-4.78 (m, 1H, D2O exchangeable), 4.90-4.00 (m, 2H), 4.00-2.22 (m, 9H), 2.20-2.00 (m, 3H), 1.60-0.60 (m, 14H); LC-MS: m/z 518.3 (M+H); HPLC: 98.64% (RT=5.997 min., method B).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washthe bed was washed with EtOH (20 mL)
  3. concentrationthe filtrate was concentrated invacuo
  4. customThe residue was purified on silica gel (100-200 mesh)

Sources & evidence

ORD record
ord-6c6b94213077461186f81b08bf1948fc
Source dataset
uspto-grants-2015_09
Patent number
US09126980B2

Reaction notes

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