Methanol → (S)-((S)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

HRID 1517816Notes

Reaction equation

HRID 1517816 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.CO>CCOC(C)=O.[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 2

HCID 887MethanolHCID 66670623(S)-((S)-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-(benzyloxycarbonylamino)propanoate

Product 1

HCID 59491006(S)-((S)-1-(4-(3-fluoro-4-(7-methoxyquinolin-4-yloxy)phenylcarbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-aminopropanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((S)-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-(benzyloxycarbonylamino)propanoate (74.7 mg, 0.1 mmol) in EtOAc (15 mL)/MeOH (10 mL) was added catalytic amount of Pd/C (10%, ˜55% w/w water content, 20 mg) under N2 atmosphere. The suspension was degassed in vacuo and purged with H2. The reaction mixture was stirred at rt for 20 min under H2 balloon. Then the mixture was filtered and the solid was washed with MeOH (5 mL×3). The filtrate was used for the next step immediately.

Workup

  1. customThe suspension was degassed in vacuo
  2. custompurged with H2
  3. filtrationThen the mixture was filtered
  4. washthe solid was washed with MeOH (5 mL×3)

Sources & evidence

ORD record
ord-a68bf84f3b884fb18d9b1a5429f9ffe1
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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