Trifluoroacetic acid → HCID 71599599, compound

HRID 882123Notes

Reaction equation

HRID 882123 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:10]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][N:15](COCC[Si](C)(C)C)[C:11]=3[N:12]=[CH:13][N:14]=2)[CH:6]=[C:5]([NH:31][C:32](=[O:36])[C:33]([CH3:35])=[CH2:34])[N:4]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[C:10]3[C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][NH:15][C:11]=3[N:12]=[CH:13][N:14]=2)[CH:6]=[C:5]([NH:31][C:32](=[O:36])[C:33]([CH3:35])=[CH2:34])[N:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89629963HCID 89629963, compound

Product 1

HCID 71599599HCID 71599599, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To ethyl 4-{2-methoxy-6-[(2-methylacryloyl)amino]pyridine-4-yl}-7-{[2 (trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (20 mg, 0.039 mmol) in DCM (0.50 mL) was added TFA (500 μL, 6.49 mmol) and the reaction was stirred for 2 hours at room temperature. The reaction was then concentrated in vacuo, and the residue dissolved in acetonitrile (1.0 mL) and ammonium hydroxide (1.0 mL) was added. The reaction was stirred for an additional 1 hour at room temperature before being concentrated in vacuo and purified by reverse phase HPLC using an acetonitrile gradient in water with 0.1% TFA modifier. The products were collected and lyophilized to afford a colorless solid. LRMS calcd for C19H20N5O4[M+H]+: 382, found 382. 1H NMR (600 MHz, DMSO-D6) δ 13.08 (bs, 1H), 10.05 (s, 1H), 8.92 (s, 1H), 8.33 (d, 1H, J=3.1 Hz), 7.87 (d, 1H, J=0.9 Hz), 6.67 (d, 1H, J=1.1 Hz), 5.87 (s, 1H), 5.52 (s, 1H), 3.90 (q, 2H, J=7.2 Hz), 3.89 (s, 3H), 1.91 (s, 3H), 0.92 (t, 3H, J=7.2 Hz).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue dissolved in acetonitrile (1.0 mL)
  3. additionammonium hydroxide (1.0 mL) was added
  4. stirringThe reaction was stirred for an additional 1 hour at room temperature
  5. concentrationbefore being concentrated in vacuo
  6. custompurified by reverse phase HPLC
  7. customThe products were collected
  8. customto afford a colorless solid

Sources & evidence

ORD record
ord-9bb98efe689941f2a22f0780c2b45d46
Source dataset
uspto-grants-2015_03
Patent number
US08993756B2

Reaction notes

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