Trifluoroacetic acid → HCID 57886042, compound

HRID 1819075Notes

Reaction equation

HRID 1819075 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]#[C:10][C:11]1[CH:29]=[N:28][C:14]2[NH:15][CH2:16][CH2:17][N:18]([CH2:19][C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=3[Cl:27])[C:13]=2[CH:12]=1)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:27][C:21]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:20]=1[CH2:19][N:18]1[CH2:17][CH2:16][NH:15][C:14]2[N:28]=[CH:29][C:11]([C:10]#[C:9][CH2:8][NH2:7])=[CH:12][C:13]1=2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 57886063HCID 57886063, compound

Product 1

HCID 57886042HCID 57886042, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

{3-[1-(2,5-Dichlorobenzyl)-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl]prop-2-ynyl}carbamic acid tert-butyl ester (19 mg), trifluoroacetic acid (250 μL) and CH2Cl2 (1 mL) were stirred under nitrogen at room temperature for 1.5 hours. 2 N NaOH (2 mL) and CH2Cl2 (approx. 10 mL) were added. The organic phase was isolated, washed twice with H2O, washed once with brine, dried over sodium sulfate, filtered and then purified by normal phase column chromatography, eluting with 5% methanol in methylene chloride, to give the title compound as an off-white solid (37% yield). M.p.=183° C., LCMS: m/z=347.35 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 3.42 (2H, t, J=4.8 Hz), 3.61 (4H, m), 4.41 (2H, s), 5.04 (1H, bs), 6.42 (1H, s), 7.21 (2H, m), 7.34 (1H, d, J=8.3 Hz), 7.59 (1H, s, J=1.0 Hz).

Workup

  1. customThe organic phase was isolated
  2. washwashed twice with H2O
  3. washwashed once with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. custompurified by normal phase column chromatography
  7. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-da27b9bc335748ecacc1fd96da26bca7
Source dataset
uspto-grants-2009_10
Patent number
US07601716B2

Reaction notes

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