Trifluoroacetic acid → HCID 57886042, compound

HRID 2074641Notes

Reaction equation

HRID 2074641 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-7a1dc8b8da5a44f3a52d73664ba7e8b2
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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