HCID 86679285, compound → HCID 71598730, compound

HRID 1519722Notes

Reaction equation

HRID 1519722 reaction equation
C([O:8][NH:9][C:10](=[O:42])[C@@:11]([CH3:41])([N:16]([CH3:40])[C:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1)=[O:18])[C:12]([NH:14][CH3:15])=[O:13])C1C=CC=CC=1.[H][H]>[Pd].CO>[OH:8][NH:9][C:10](=[O:42])[C@@:11]([CH3:41])([N:16]([CH3:40])[C:17]([C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:35][CH2:36][O:37][CH2:38][CH2:39]3)=[CH:27][CH:26]=2)=[CH:23][CH:24]=1)=[O:18])[C:12]([NH:14][CH3:15])=[O:13]

Participants

5

Reactant 2

HCID 86679285HCID 86679285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 71598730HCID 71598730, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (5.0 mg) was added to a methanol (3.0 mL) solution of (2S)-N-(benzyloxy)-N′,2-dimethyl-2-[methyl({4′-[2-(morpholin-4-yl)ethoxy]biphenyl-4-yl}carbonyl)amino]propanediamide (27 mg) as obtained in Example 19-(5), and the mixture was stirred in a hydrogen atmosphere for 6 hours at room temperature. The reaction mixture was filtered through Celite, and the solvent was distilled off under reduced pressure. The residue was subjected to isolation and purification by LC to obtain (2S)-N-hydroxy-N′,2-dimethyl-2-[methyl({4′-[2-(morpholin-4-yl)ethoxy]biphenyl-4-yl}carbonyl)amino]propanediamide (Compound 437, light yellow solid) (8.0 mg, 35%).

Workup

  1. customas obtained in Example 19-(5)
  2. filtrationThe reaction mixture was filtered through Celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was subjected to isolation and purification by LC

Sources & evidence

ORD record
ord-53b3323feb2844c491351ad403f380a8
Source dataset
uspto-grants-2015_07
Patent number
US09073821B2

Reaction notes

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