HCID 71015501, compound → 6-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)-nicotinaldehyde

HRID 716043Notes

Reaction equation

HRID 716043 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[N:11]=[C:12]3[C:18]([C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:17][N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:13]3=[N:14][CH:15]=2)=[N:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[C:19]([C:18]1[C:12]2[C:13](=[N:14][CH:15]=[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][N:7]=3)[N:11]=2)[N:16]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:30])([CH3:32])[CH3:31])[CH:17]=1)(=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 71015501HCID 71015501, compound

Product 1

HCID 867121286-(7-pivaloyl-5-((2-(trimethylsilyl)-ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)-nicotinaldehydeYield 66.7%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 100 ml three necked round bottom flask 1-(2-(5-(hydroxymethyl)pyridin-2-ylamino)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethylpropan-1-one (0.5 g, 0.00109 mole) was taken in CH2Cl2 (20 ml). MnO2 (1.9 g, 0.0219 mole) was added in one portion at room temperature under nitrogen atmosphere. The reaction mixture was stirred for 15 min. After completion of the reaction, the reaction mixture was filtered through celite bed and washed with CH2Cl2. The filtrate was collected and concentrated to afford crude product which was subjected for the column purification. The crude compound was purified using column purification by eluting the compound with 25-30% ethyl acetate in hexanes to yield 0.33 g of 6-(7-pivaloyl-5-((2-(trimethylsilyl)ethoxy)-methyl)-5H-pyrrolo[2,3-b]pyrazin-2-ylamino)nicotinaldehyde.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite bed
  3. washwashed with CH2Cl2
  4. customThe filtrate was collected
  5. concentrationconcentrated
  6. customto afford crude product which
  7. customwas subjected for the column purification
  8. customThe crude compound was purified
  9. customcolumn purification
  10. washby eluting the compound with 25-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-67cd3f92b68e4d56b34d2f0547a45fd6
Source dataset
uspto-grants-2015_11
Patent number
US09187487B2

Reaction notes

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