(S)-((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-(benzyloxy-carbonyl-amino)propanoate → (S)-((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

HRID 1517804Notes

Reaction equation

HRID 1517804 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22]([C:24]2[C:25](=[O:55])[N:26]([C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[N:27]([CH2:30][C@H:31]([O:33][C:34](=[O:48])[C@@H:35]([NH:37]C(OCC3C=CC=CC=3)=O)[CH3:36])[CH3:32])[C:28]=2[CH3:29])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1>CCOC(C)=O.CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([NH:21][C:22]([C:24]2[C:25](=[O:55])[N:26]([C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[N:27]([CH2:30][C@H:31]([O:33][C:34](=[O:48])[C@@H:35]([NH2:37])[CH3:36])[CH3:32])[C:28]=2[CH3:29])=[O:23])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=2)[N:12]=[CH:11][CH:10]=1

Participants

5

Reactant 1

HCID 86645592(S)-((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-(benzyloxy-carbonyl-amino)propanoate

Product 1

HCID 46937494(S)-((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((R)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenyl carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-(benzyloxy-carbonyl-amino)propanoate (74.7 mg, 0.1 mmol) in a mixture of EtOAc (15 mL) and MeOH (10 mL) was added catalytic amount Pd/C (10%, ˜55% w/w water content, 20 mg) under N2 atmosphere. The suspension was degassed under vacuum and then purged with H2. The reaction mixture was stirred at rt for 20 minutes under H2 balloon. The mixture was filtered and the residue was washed with MeOH (5 mL×3). The filtrate used for the next step immediately.

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2
  3. filtrationThe mixture was filtered
  4. washthe residue was washed with MeOH (5 mL×3)

Sources & evidence

ORD record
ord-5aad5e106d4b477e87d09ebd20331980
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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