HCID 22480507, compound → HCID 22480514, compound

HRID 2182585Notes

Reaction equation

HRID 2182585 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:43])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH3:42])=[C:31]([Cl:44])[CH:30]=2)=[C:6]([NH:8][C:9](=[O:27])[O:10][CH2:11][O:12][C:13](=[O:26])[CH2:14][CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH:7]=1>O1CCCC1.[Pd]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35](=[O:43])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[CH3:42])=[C:31]([Cl:44])[CH:30]=2)=[C:6]([NH:8][C:9](=[O:27])[O:10][CH2:11][O:12][C:13](=[O:26])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:7]=1

Participants

4

Reactant 1

HCID 22480507HCID 22480507, compound2×

Product 1

HCID 22480514HCID 22480514, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1-(3-(Benzyloxycarbonyl)propanoyloxy)methyl N-[5-bromo-2-[3-chloro-4-(2-methylbenzoyl)-phenylamino]phenyl]carbamate (Compound 212) (580 mg, 0.9 mmol) was dissolved in tetrahydrofurane (50 ml), 10% Pd on carbon (200 mg) was added, and the reaction mixture was hydrogenated (1 atm) under vigorously shaken until no more starting material remained, as seen on TLC. The reaction mixture was purified by chromatography using a mixture of methanol/chloroform 1:9 to give the title compound.

Workup

  1. customThe reaction mixture was purified by chromatography
  2. additiona mixture of methanol/chloroform 1:9

Sources & evidence

ORD record
ord-c3cd2520f7dd41c18ec0d6826c58fd5c
Source dataset
uspto-grants-2005_05
Patent number
US06897236B1

Reaction notes

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