Tetrahydrofuran → HCID 135971874, compound

HRID 1469917Notes

Reaction equation

HRID 1469917 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-cb9b4618b6e04f7c8578cd89edbc8cef
Source dataset
uspto-grants-2015_04
Patent number
US09006277B2

Reaction notes

Loading…