Trifluoroacetic acid → HCID 9920895, compound

HRID 1835184Notes

Reaction equation

HRID 1835184 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[CH:8]=[C:9]([C:13]2[NH:21][C:16]3=[N:17][CH:18]=[CH:19][N:20]=[C:15]3[CH:14]=2)[CH:10]=[CH:11][CH:12]=1.FC(F)(F)C(O)=O>ClCCl>[N:20]1[CH:19]=[CH:18][N:17]=[C:16]2[NH:21][C:13]([C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[CH:2]=[O:1])=[CH:14][C:15]=12

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22477461HCID 22477461, compound

Product 1

HCID 9920895HCID 9920895, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(3-[1,3]dioxan-2-yl-phenyl)-5H-pyrrolo[2,3-b]pyrazine [1.6 g, Example 1(g)] in dichloromethane (50 mL) was treated with trifluoroacetic acid (5 mL). The resultant mixture was heated at reflux for 6 hours, then allowed to cool overnight and then evaporated. The residue was triturated with diethyl ether to give a yellow solid which was recrystallised from ethyl acetate to give the title compound (0.6 g) as a yellow crystalline solid, m.p. 268-270° C. [Elemental analysis: C, 69.96; H, 3.92; N,18.69%. Calculated for C13H9N3O: C, 69.95; H, 4.06; N, 18.82%].

Workup

  1. temperatureat reflux for 6 hours
  2. temperatureto cool overnight
  3. customevaporated
  4. customThe residue was triturated with diethyl ether
  5. customto give a yellow solid which
  6. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-b573fdbdad8c4878a9441442746f3be8
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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