Water → HCID 10126703, compound

HRID 895133Notes

Reaction equation

HRID 895133 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.C1CCC(N=C=NC2CCCCC2)CC1.[F:25][C:26]1[CH:27]=[C:28]([N:38]2[CH:42]=[C:41]([CH2:43][NH2:44])[N:40]=[N:39]2)[CH:29]=[CH:30][C:31]=1[N:32]1[CH2:37][CH2:36][S:35][CH2:34][CH2:33]1.O>C(#N)C>[F:25][C:26]1[CH:27]=[C:28]([N:38]2[CH:42]=[C:41]([CH2:43][NH:44][C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[O:9])[N:40]=[N:39]2)[CH:29]=[CH:30][C:31]=1[N:32]1[CH2:33][CH2:34][S:35][CH2:36][CH2:37]1

Participants

6

Reactant 4

HCID 962WaterHCID 10472-Pyrazinecarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 10214862HCID 10214862, compound

Product 1

HCID 10126703HCID 10126703, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of pyrazine-2-carboxylic acid (127 mg, 1.02 mmol) and DCC (211 mg, 1.02 mmol) in acetonitrile (5 mL) was added to a stirring solution of C-[1-(3-fluoro-4-thiomorpholin-4-yl-phenyl)-1H-[1,2,3]triazol-4-yl]-methylamine (200 mg, 0.68 mmol), obtained in Example 19, in dry acetonitrile (10 mL) and allowed to stir at room temperature for 6 h. The reaction mixture was then poured into ice-cooled water and extracted with ethyl acetate (20 mL×2). The organic portion was washed with water followed by brine and dried over sodium sulfate. Upon concentration and purification by silica gel column chromatography (acetone/chloroform, 15:85) the title compound was obtained (245 mg, 90%). Mp. 216-218° C.

Workup

  1. additionThe reaction mixture was then poured into ice-
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. washThe organic portion was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationUpon concentration and purification by silica gel column chromatography (acetone/chloroform, 15:85) the title compound
  6. customwas obtained (245 mg, 90%)

Sources & evidence

ORD record
ord-8d2f44cf80ae4a9686bc115a0ed5dd31
Source dataset
uspto-grants-2005_07
Patent number
US06914058B2

Reaction notes

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