Acetic Acid → HCID 58010206, compound

HRID 1628059Notes

Reaction equation

HRID 1628059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH2:22])[N:20]=[C:15]2[CH:14]=1.N1C=CC=CC=1.[CH3:38][C:39](OC(C)=O)=[O:40].CC(O)=O>C1COCC1.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[CH:7]=[C:6]2[C:13]1[N:23]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:16]2=[N:17][CH:18]=[C:19]([CH2:21][NH:22][C:39](=[O:40])[CH3:38])[N:20]=[C:15]2[CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 58009787HCID 58009787, compound

Product 1

HCID 58010206HCID 58010206, compoundYield 102%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanamine (0.185 g, 0.423 mmol, Preparation #I.1) in THF (5 mL) was treated with pyridine (0.044 mL, 0.55 mmol) and Ac2O (0.044 mL, 0.46 mmol). After about 5 min the mixture was treated with AcOH (0.024 mL, 0.42 mmol), diluted with EtOAc (20 mL) and then washed with water (15 mL) and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and evaporated under reduced pressure to give N-((6-(5-Methoxy-1-methyl-1H-indol-3-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)methyl)acetamide (0.207 g, 102%, crude): LC/MS (Table 2, Method a) Rt=2.63 min; MS m/z 480 (M+H)+.

Workup

  1. washwashed with water (15 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d427ff65584143b19196ad92795e5c23
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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