Tetrahydrofuran → HCID 135971874, compound

HRID 76106Notes

Reaction equation

HRID 76106 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([C:35]2[CH:36]=[C:37]3[C:41](=[CH:42][CH:43]=2)[N:40]([CH3:44])[CH:39]=[CH:38]3)[C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][N:30]=1)C1C=CC=CC=1.O1CCCC1>[Pd].[OH-].[Pd+2].[OH-].CO>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]1[N:27]([C:35]2[CH:36]=[C:37]3[C:41](=[CH:42][CH:43]=2)[N:40]([CH3:44])[CH:39]=[CH:38]3)[C:28]([NH:31][C:32](=[O:34])[CH3:33])=[N:29][N:30]=1

Participants

6

Reactant 2

HCID 8028TetrahydrofuranHCID 66986539N-(5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)acetamide

Product 1

HCID 135971874HCID 135971874, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A flask was charged with N-(5-(2,4-bis(benzyloxy)-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)acetamide, tetrahydrofuran (10 mL), methanol (10 mL), 10% palladium on carbon (50 mg.) (in some cases palladium hydroxide was used). The reaction was stirred under an atmosphere of hydrogen for 16 hours, filtered through celite, and evaporated to give N-(5-(2,4-dihydroxy-5-isopropylphenyl)-4-(1-methyl-1H-indol-5-yl)-4H-1,2,4-triazol-3-yl)acetamide. 1H-NMR (CDCl3): 8.60 (br, 1H); 7.60 (d, 1H); 7.49 (d, 1H); 7.29 (br, 1H); 7.23 (d, 1H); 7.14 (dd, 1H); 6.55 (d, 1H); 6.40 (s, 1H); 6.38 (s, 1H); 3.94 (s, 3H); 2.82 (q, 1H); 2.20 (s, 3H); 0.47 (d, 6H). MS: expected ion=406.2; observed ion=406.3.

Workup

  1. filtrationfiltered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-b49e3833f46e46e1b5258b38dfc5c9d8
Source dataset
uspto-grants-2014_09
Patent number
US08835464B2

Reaction notes

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