HCID 68313002, compound → HCID 68312697, compound

HRID 1530441Notes

Reaction equation

HRID 1530441 reaction equation
C([O:8][CH2:9][CH2:10][C:11]([O:15][C:16]1[CH:38]=[CH:37][C:19]2[C:20]3[N:24]([CH2:25][CH2:26][O:27][C:18]=2[CH:17]=1)[CH:23]=[C:22]([C:28]1[N:29]([CH:34]([CH3:36])[CH3:35])[N:30]=[C:31]([CH3:33])[N:32]=1)[N:21]=3)([CH3:14])[CH2:12][OH:13])C1C=CC=CC=1>[Pd].[OH-].[OH-].[Pd+2]>[CH:34]([N:29]1[C:28]([C:22]2[N:21]=[C:20]3[N:24]([CH2:25][CH2:26][O:27][C:18]4[CH:17]=[C:16]([O:15][C:11]([CH3:14])([CH2:10][CH2:9][OH:8])[CH2:12][OH:13])[CH:38]=[CH:37][C:19]=43)[CH:23]=2)=[N:32][C:31]([CH3:33])=[N:30]1)([CH3:36])[CH3:35]

Participants

4

Reactant 1

HCID 68313002HCID 68313002, compound

Product 1

HCID 68312697HCID 68312697, compoundYield 57.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalyst

Procedure

To a solution of 4-benzyloxy-2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylbutan-1-ol (29 mg, 0.0568 mmol) in IMS (5 mL) was added 10% Pd/C (5 mg). The reaction mixture was stirred at RT under a hydrogen atmosphere for 4 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. To a solution of the residue thus obtained in IMS (5 mL) was added Pd(OH)2/C (10 mg) and the reaction mixture was stirred at RT under a hydrogen atmosphere for 18 h. The suspension was then filtered through a pad of Celite® and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM) affording 2-[2-(2-Isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylbutane-1,4-diol as a colorless gum (14 mg, 56%). LCMS: RT 2.39 min [M+H]+ 428.3

Workup

  1. filtrationThe suspension was then filtered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customTo a solution of the residue thus obtained in IMS (5 mL)
  4. stirringthe reaction mixture was stirred at RT under a hydrogen atmosphere for 18 h
  5. filtrationThe suspension was then filtered through a pad of Celite®
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM)

Sources & evidence

ORD record
ord-3198ea4b240e425486c4751ba40be9f3
Source dataset
uspto-grants-2015_07
Patent number
US09090628B2

Reaction notes

Loading…