HCID 68534911, compound → HCID 135507469, compound

HRID 1816952Notes

Reaction equation

HRID 1816952 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:20]3[N:21]=[C:22]([NH:24][C:25]([NH:27][C@@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[O:26])[N:23]=[C:19]3[N:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[C].[Pd]>[CH3:35][C@H:28]([NH:27][C:25]([NH:24][C:22]1[N:23]=[C:19]2[N:18]=[CH:17][CH:16]=[C:15]([C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=3)[N:20]2[N:21]=1)=[O:26])[CH2:29][CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34]

Participants

5

Reactant 2

HCID 68534911HCID 68534911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135507469HCID 135507469, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

(S)-1-[7-(4-benzyloxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]-3-(1,5-dimethylhexyl)urea (the compound obtained in Example 245; 7.1 g) and palladium carbon (50% water content; 2.0 g) were suspended in acetic acid (570 ml), and the obtained suspension was stirred in a hydrogen atmosphere at a room temperature for 5 days. Thereafter, the reaction solution was filtrated with a filter medium (Celite), and the collected product was then washed with methanol. The filtrate and the washing solution were mixed, and the obtained mixture was then concentrated under a reduced pressure. The obtained residue was dissolved in methylene chloride (150 ml), and the obtained solution was washed with a saturated saline solution (100 ml) twice. The saturated saline solution layer obtained after the second washing was extracted with methylene chloride (70 ml×3). The organic layers were gathered, and the obtained layer was then concentrated under a reduced pressure. The obtained residue was purified by silica gel column chromatography (eluted with 1% to 2% methanol-containing methylene chloride) to obtain the captioned compound (4.72 g).

Workup

  1. filtrationThereafter, the reaction solution was filtrated with a filter medium (Celite)
  2. washthe collected product was then washed with methanol
  3. additionThe filtrate and the washing solution were mixed
  4. concentrationthe obtained mixture was then concentrated under a reduced pressure
  5. dissolutionThe obtained residue was dissolved in methylene chloride (150 ml)
  6. washthe obtained solution was washed with a saturated saline solution (100 ml) twice
  7. customThe saturated saline solution layer obtained after the
  8. washsecond washing
  9. extractionwas extracted with methylene chloride (70 ml×3)
  10. concentrationthe obtained layer was then concentrated under a reduced pressure
  11. customThe obtained residue was purified by silica gel column chromatography (eluted with 1% to 2% methanol-containing methylene chloride)

Sources & evidence

ORD record
ord-801a1d9fd53543458516a53d329ac1c2
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

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