THIAZOL-2-YL-ACETONITRILE → HCID 77981592, compound

HRID 716059Notes

Reaction equation

HRID 716059 reaction equation
[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[S:33]1[CH:37]=[CH:36][N:35]=[C:34]1[CH2:38][C:39]#[N:40].C(O)(=O)C.N1CCCCC1>C(O)C>[C:1]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH:21]=[C:38]([C:34]4[S:33][CH:37]=[CH:36][N:35]=4)[C:39]#[N:40])=[CH:23][CH:24]=3)[N:14]=2)[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:31])([CH3:32])[CH3:30])[CH:8]=1)(=[O:6])[C:2]([CH3:4])([CH3:3])[CH3:5]

Participants

5

Reactant 3

HCID 4913352THIAZOL-2-YL-ACETONITRILEHCID 9793820Piperidine, acetateHCID 867121234-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde

Product 1

HCID 77981592HCID 77981592, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a 25 ml three necked round bottom flask, 4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)benzaldehyde (0.1 g, 0.000221 mol) and 2-(thiazol-2-yl)acetonitrile (0.082 g, 0.000663 mol) were taken in ethanol (5 ml). Piperidine acetate (3.3 M solution in water) (0.2 ml) was added dropwise at RT. After completion of the addition, reaction mixture was refluxed overnight and ethanol was distilled out and water was added to residue. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, dried over Na2SO4, filtered and concentrated to afford crude product. The crude compound was triturated with n-pentane, the pentane layer was decanted and solid was dried under vacuum to yield 0.090 g of 3-(4-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)phenyl)-2-(thiazol-2-yl)acrylonitrile.

Workup

  1. additionAfter completion of the addition, reaction mixture
  2. temperaturewas refluxed overnight
  3. distillationethanol was distilled out and water
  4. additionwas added to residue
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford crude product
  10. customThe crude compound was triturated with n-pentane
  11. customthe pentane layer was decanted
  12. customsolid was dried under vacuum

Sources & evidence

ORD record
ord-56ef3a42deea4892b1a7adc3eb092ac6
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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