Trifluoroacetic acid → HCID 136386510, compound

HRID 1821891Notes

Reaction equation

HRID 1821891 reaction equation
[C:1]1([C:7](=[N:17][O:18][CH2:19][CH2:20][NH:21]C(=O)OC(C)(C)C)[C:8]2[C:16]3[C:11](=[CH:12][N:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:21][CH2:20][CH2:19][O:18][N:17]=[C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]1[C:16]2[C:11](=[CH:12][N:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136365981HCID 136365981, compound

Product 1

HCID 136386510HCID 136386510, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-[[[phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methylene]amino]oxy]ethylcarbamate (Example 111) (385.8 mg, 0.94 mmol), trifluoroacetic acid (4 mL) and methylene chloride (2 mL) was stirred at room temperature for 6 h. The solvent was removed in vacuo. The crude material was purified and free based using SCX-2 to give phenyl(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone O-(2-aminoethyl)oxime (220 mg, 84%) as an off-white foam: 1H NMR (500 MHz, CD3OD) δ2.97-3.02 (2H, m), 3.20-3.31 (2H, m), 6.75-6.77 (0.6H, m), 7.19 (0.4H, m), 7.40-7.49 (5H, m), 7.91-7.92 (0.6H, m), 8.07-8.20 (1.5H, m), 8.70-8.72 (1H, m); ESI MS m/z 281 [C16H16N4O+H]+; HPLC (Method A) >99% (AUC), Isomeric ratio 58:42, tR=12.5 and 12.2 min.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe crude material was purified

Sources & evidence

ORD record
ord-859c0d078aef4394913e50c9ec706998
Source dataset
uspto-grants-2009_10
Patent number
US07608627B2

Reaction notes

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