HCID 68536788, compound → HCID 136330237, compound

HRID 1816950Notes

Reaction equation

HRID 1816950 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]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[CH3:29])=[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]>[OH: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]([C:30]4[CH:35]=[CH:34][CH:33]=[C:32]([O:36][CH3:37])[CH:31]=4)[CH3:29])=[O:26])[N:23]=[C:19]3[N:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 68536788HCID 68536788, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 136330237HCID 136330237, 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-(3-methoxyphenyl)ethyl]urea (the compound obtained in Example 222; 7.83 g) was dissolved in acetic acid (600 ml). Thereafter, 10% palladium carbon (50% water content; 2.0 g) was added to the solution, and the obtained mixture was stirred at 40° C. overnight in a hydrogen atmosphere. The reaction solution was filtrated with a filter medium (Celite), and the resultant was then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (eluted with 4% methanol-containing methylene chloride) to obtain the captioned compound (5.37 g).

Workup

  1. filtrationThe reaction solution was filtrated with a filter medium (Celite)
  2. concentrationthe resultant was then concentrated under a reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluted with 4% methanol-containing methylene chloride)

Sources & evidence

ORD record
ord-e5758ae9890844bc8cb3a8397cb1ddec
Source dataset
uspto-grants-2009_10
Patent number
US07598244B2

Reaction notes

Loading…