HCID 57388228, compound → HCID 136378686, compound

HRID 2278577Notes

Reaction equation

HRID 2278577 reaction equation
[N:1]1([C:7]2[N:8]=[C:9]([CH2:14][C:15]([O-:17])=O)[NH:10][C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Na+].[Cl:19][C:20]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH:23]([CH3:30])[NH:24]2>>[Cl:19][C:20]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH2:22][CH:23]([CH3:30])[N:24]2[C:15](=[O:17])[CH2:14][C:9]1[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]2[CH2:2][CH2:3][O:4][CH2:5][CH2:6]2)[N:8]=1

Participants

3

Reactant 2

HCID 57388228HCID 57388228, compoundHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378686HCID 136378686, compoundYield 44.8%

Procedure

The product is prepared according to the procedure described in example 1c, step 3c, using 248 mg of sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate and 160 mg of 4-chloro-5-fluoro-2-methyl-2,3-dihydro-1H-indole (reference example 10c). After silica column purification: eluent 99/01 then 98/02 dichloromethane/methanol, 157 mg of 2-[2-(4-chloro-5-fluoro-2-methyl-2,3-dihydroindol-1-yl)-2-oxoethyl]-6-morpholin-4-yl-3H-pyrimidin-4-one are obtained in the form of a solid which will be separated into its two enantiomers on a chiral column.

Workup

  1. customThe product is prepared
  2. customAfter silica column purification

Sources & evidence

ORD record
ord-e08263e879a94268abec754568ffef79
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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