HCID 67429973, compound → HCID 25204456, compound

HRID 1661089Notes

Reaction equation

HRID 1661089 reaction equation
[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[C:29](Cl)[CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][N:33]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:32]2=[O:44])=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>[Pd].O1CCOCC1>[CH2:1]([C@H:8]([NH:24][C:25]([C:27]1[CH:28]=[CH:29][CH:30]=[C:31]2[C:36]=1[N:35]=[CH:34][N:33]([CH:37]([CH2:41][CH2:42][CH3:43])[CH2:38][CH2:39][CH3:40])[C:32]2=[O:44])=[O:26])[C@H:9]([OH:23])[CH2:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67429973HCID 67429973, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 25204456HCID 25204456, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

195 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]-amino}propyl]-6-chloro-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide, 5 cm3 of dioxane and 30 mg of 10% (50% wet with water) palladium on carbon are stirred under 10 bar of hydrogen in an autoclave. Since the reaction does not develop, 30 mg of 10% dry palladium on carbon are added and the reaction mixture is stirred under 15 bar of hydrogen in an autoclave. The catalyst is filtered and the filtrate is concentrated under reduced pressure (5 kPa). 185 mg of N-[(1S,2R)-1-benzyl-2-hydroxy-3-{[3-(trifluoromethyl)benzyl]amino}propyl]-4-oxo-3-(1-propylbutyl)-3,4-dihydroquinazoline-8-carboxamide are obtained.

Workup

  1. filtrationThe catalyst is filtered
  2. concentrationthe filtrate is concentrated under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-691e2162a79c42969e3d42226b480cc0
Source dataset
uspto-grants-2011_10
Patent number
US08030320B2

Reaction notes

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