HCID 11854452, compound → HCID 11854453, compound

HRID 1162907Notes

Reaction equation

HRID 1162907 reaction equation
C([O:8][CH2:9][C@H:10]1[CH2:14][N:13]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:35])([F:34])[F:33])[NH:21][C:22]3=[O:25])=[CH:17][CH:16]=2)[C:12](=[O:36])[N:11]1[CH3:37])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][CH2:9][C@H:10]1[CH2:14][N:13]([C:15]2[CH:24]=[C:23]3[C:18]([CH:19]=[C:20]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:32]([F:33])([F:35])[F:34])[NH:21][C:22]3=[O:25])=[CH:17][CH:16]=2)[C:12](=[O:36])[N:11]1[CH3:37]

Participants

5

Reactant 2

HCID 11854452HCID 11854452, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11854453HCID 11854453, compoundYield 104.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The 7-((R)-4-benzyloxymethyl-3-methyl-2-oxoimidazolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (13 mg, 0.025 mmol) prepared in Example 1-35 was dissolved in methanol (5 ml). Thereafter, 10% Pd—C (3 mg) was added to the obtained solution, and the obtained mixture was then stirred in a hydrogen atmosphere for 3 hours. The reaction solution was filtered through celite, and the filtrate was then concentrated. The obtained residue was purified by silica gel TLC used for preparative separation (dichloromethane:methanol=20:1), so as to obtain 7-((R)-4-hydroxymethyl-3-methyl-2-oxoimidazolidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (10.9 mg, quantitative) in the form of a white solid.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was then concentrated
  3. customThe obtained residue was purified by silica gel TLC
  4. customused for preparative separation (dichloromethane:methanol=20:1)

Sources & evidence

ORD record
ord-899c5ed1f73f4e0f87c2cf8244c6aab1
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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