Trifluoroacetic acid → HCID 57886042, compound

HRID 659420Notes

Reaction equation

HRID 659420 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-b70fd121effa4ae49892e1b3e56b4231
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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