2-Aminobenzonitrile → HCID 178507210, compound

HRID 395350Notes

Reaction equation

HRID 395350 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]3[N:13]=[C:14]([CH2:16][C:17]([O:19]CC)=O)[NH:15][C:10]3=[CH:9][CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]#[N:30]>>[NH2:30][C:29]1[C:24]2[C:23](=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:22][C:17](=[O:19])[C:16]=1[C:14]1[NH:13][C:11]2=[N:12][C:7]([N:1]3[CH2:2][CH2:3][O:4][CH2:5][CH2:6]3)=[CH:8][CH:9]=[C:10]2[N:15]=1

Participants

3

Reactant 2

HCID 729132-AminobenzonitrileHCID 22664674HCID 22664674, compound

Product 1

HCID 178507210HCID 178507210, compound

Procedure

The title compound was synthesized as described in Example 45, Method E using ethyl 2-(5-morpholin-4-ylimidazolo[5,4-b]pyridin-2-yl)acetate and 2-aminobenzenecarbonitrile, with a modified workup procedure. After quenching with a saturated aqueous ammonium chloride solution, the two phases were separated and the aqueous phase extracted with EtOAc. Upon standing, a solid formed and precipitated out of the organic extracts. The precipitate, a dark brown solid, was filtered off and dried. Purification by reverse phase chromatography afforded the desired product as a reddish solid. LC/MS m/z 363.2 (MH+), Rf 2.20 minutes.

Workup

  1. customThe title compound was synthesized
  2. customAfter quenching with a saturated aqueous ammonium chloride solution
  3. customthe two phases were separated
  4. extractionthe aqueous phase extracted with EtOAc
  5. customa solid formed
  6. customprecipitated out of the organic extracts
  7. filtrationThe precipitate, a dark brown solid, was filtered off
  8. customdried
  9. customPurification by reverse phase chromatography

Sources & evidence

ORD record
ord-32060f59face4359aa9f59f3d7fec8d1
Source dataset
uspto-grants-2003_08
Patent number
US06605617B2

Reaction notes

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