HCID 66762054, compound → HCID 66763583, compound

HRID 578667Notes

Reaction equation

HRID 578667 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][C@@H:13]([NH:20][C:21]1[C:30]2[C:25](=[C:26]([C:31](=[O:33])[NH2:32])[CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C1C=CC=CC=1>CCO.[Pd]>[NH2:10][CH2:11][CH2:12][CH:13]([NH:20][C:21]1[C:30]2[C:25](=[C:26]([C:31]([NH2:32])=[O:33])[CH:27]=[CH:28][CH:29]=2)[N:24]=[CH:23][N:22]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 66762054HCID 66762054, compound

Product 1

HCID 66763583HCID 66763583, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

[(R)-3-(8-Carbamoyl-quinazolin-4-ylamino)-3-phenyl-propyl]-carbamic acid benzyl ester (20 mg, 0.04 mmol) was dissolved in EtOH (5 mL) and treated with 5% Pd/C under 1 atm of H2. Upon completion the reaction was filtered through a pad of celite, and the pad was washed with EtOH. The crude material was purified by silica gel (10% MeOH/CH2Cl2) to afford the desired compound (7 mg, 50%). LCMS (ESI) 322 (M+H)

Workup

  1. filtrationUpon completion the reaction was filtered through a pad of celite
  2. washthe pad was washed with EtOH
  3. customThe crude material was purified by silica gel (10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-a1d20baf37d849f298b30cd68574ea95
Source dataset
uspto-grants-2015_05
Patent number
US09040560B2

Reaction notes

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