5-Amino-2-fluorobenzonitrile → HCID 136041738, compound

HRID 1631571Notes

Reaction equation

HRID 1631571 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+].[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([F:28])=[C:24]([CH:27]=1)[C:25]#[N:26]>>[C:25]([C:24]1[CH:27]=[C:20]([NH:19][C:15](=[O:17])[CH2:14][C:9]2[NH:10][C:11](=[O:13])[CH:12]=[C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)[N:8]=2)[CH:21]=[CH:22][C:23]=1[F:28])#[N:26]

Participants

3

Reactant 2

HCID 27376735-Amino-2-fluorobenzonitrileHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136041738HCID 136041738, compoundYield 22.7%

Procedure

The product is prepared according to the procedure described in Example 19, using 261 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of Example 1 and 163 mg of 5-amino-2-fluorobenzonitrile in place of the 3-(tert-butyl)aniline. The reaction mixture is concentrated to dryness under reduced pressure and the residue is then purified by silica column chromatography, elution being carried out with a gradient of the eluent CH2Cl2/MeOH: 90/10 in dichloromethane of 0% to 100%. 81 mg of N-(3-cyano-4-fluorophenyl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the form of an amber solid, the characteristics of which are the following:

Workup

  1. customThe product is prepared
  2. concentrationThe reaction mixture is concentrated to dryness under reduced pressure
  3. customthe residue is then purified by silica column chromatography, elution

Sources & evidence

ORD record
ord-692f1da8e96744119d9e86251311c779
Source dataset
uspto-grants-2014_07
Patent number
US08791255B2

Reaction notes

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