HCID 57388226, compound → HCID 136378668, compound

HRID 2278501Notes

Reaction equation

HRID 2278501 reaction equation
[F:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]([O-:12])=O)=[N:4][C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[Na+].[CH3:20][CH:21]1[CH2:29][C:28]2[C:23](=[CH:24][C:25]([F:30])=[CH:26][CH:27]=2)[NH:22]1>>[F:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]([N:22]2[C:23]3[C:28](=[CH:27][CH:26]=[C:25]([F:30])[CH:24]=3)[CH2:29][CH:21]2[CH3:20])=[O:12])=[N:4][C:3]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 57388226HCID 57388226, compoundHCID 136069585Sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136378668HCID 136378668, compoundYield 46.2%

Procedure

The product is prepared by following the procedure described in example 1a (step 5a) using 123 mg of sodium (5-fluoro-4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate obtained in step 2a of example 6a and 62 mg of (−)-2-methyl-6-fluoro-2,3-dihydro-1H-indole (reference example 6a). After silica column purification: eluent 98/02 dichloromethane/methanol, 74 mg of 5-fluoro-2-[2-((+)-6-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, the characteristics of which are the following:

Workup

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

Sources & evidence

ORD record
ord-0cd0700b650044a983fce3254c0abf36
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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