HCID 67582985, compound → HCID 57264566, compound

HRID 1416475Notes

Reaction equation

HRID 1416475 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:26]=[C:25]([O:27][C@@H:28]3[CH2:32][C@H:31]([OH:33])[C@@H:30]([OH:34])[C@H:29]3[OH:35])[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[OH:35][C@@H:29]1[C@H:30]([OH:34])[C@@H:31]([OH:33])[CH2:32][C@H:28]1[O:27][C:25]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=[C:17]([N:14]2[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]2)[N:26]=1

Participants

4

Reactant 1

HCID 67582985HCID 67582985, compound

Product 1

HCID 57264566HCID 57264566, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-[4-(benzyloxycarbonyl)piperazin-1-yl]-4-[(1R,2R,3R,4S)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]quinazoline (854 mg) in methanol (15 ml) is added 10% palladium/carbon (200 mg), and the mixture is stirred under hydrogen atmosphere and under atmospheric pressure at room temperature for 14.5 hours. The reaction mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure to give 4-[(1R,2R,3R,4S)-(2,3,4-trihydroxycyclopentan-1-yl)oxy]-2-(1-piperazinyl)quinazoline (545 mg) as foam.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-a0420c28c5c848db84be188181bce58e
Source dataset
uspto-grants-1999_06
Patent number
US05912247

Reaction notes

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