HCID 23630907, compound → HCID 11154664, compound

HRID 917726Notes

Reaction equation

HRID 917726 reaction equation
[NH2:1][C:2]([C:4]1[C:5]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[CH:6][C:7](=[O:18])[N:8]([CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[CH:9]=1)=[O:3]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:1][C:2]([C:4]1[C:5]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[CH:6][C:7](=[O:18])[N:8]([CH2:10][C:11]([OH:13])=[O:12])[CH:9]=1)=[O:3]

Participants

4

Reactant 1

HCID 23630907HCID 23630907, compound

Product 1

HCID 11154664HCID 11154664, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (5-(aminocarbonyl)-4-(2-fluoro-4-iodoanilino)-2-oxo-1(2H)-pyridinyl)acetate (225 mg, 0.46 mmol) was dissolved in a mixture of CH2Cl2 (10 mL) and trifluoroacetic acid (10 mL) and stirred at R.T. for 2 h. All solvent was evaporated under a stream of nitrogen and the resulting oil was redissolved in MeOH (10 mL) to which was added sat. NaHCO3 (10 mL). This mixture was stirred at R.T for 1 h. then 1 M HCl (50 mL) added and the resulting white precipitate collected by filtration. Purification was carried out by recrystallisation from EtOAc/MeOH to afford (5-(aminocarbonyl)-4-(2-fluoro-4-iodoanilino)-2-oxo-1(2H)-pyridinyl)acetic acid as a white solid (76 mg, 38%), m.p. (EtOAc/MeOH) 296-300° C. 1H NMR [(CD3)2SO, 400 MHz] δ 13.10 (v br s, 1H), 10.42 (s, 1H), 8.32 (s, 1H), 7.86 (br s, 1H), 7.75 (dd, J=10.2, 1.9 Hz, 1H), 7.58 (dd, J=8.4, 0.8 Hz, 1H), 7.52 (br s, 1H), 7.30 (t, J=8.5 Hz, 1H), 5.53 (d, J=1.0 Hz, 1H), 4.49 (s, 2H). Anal. Calcd for C14H11FIN3O4.0.5H2O: C, 38.2; H, 2.7; N, 9.5. Found: C, 38.0; H, 2.4; N, 9.1.

Workup

  1. customAll solvent was evaporated under a stream of nitrogen
  2. dissolutionthe resulting oil was redissolved in MeOH (10 mL) to which
  3. additionwas added sat. NaHCO3 (10 mL)
  4. stirringThis mixture was stirred at R.T for 1 h.
  5. addition1 M HCl (50 mL) added
  6. filtrationthe resulting white precipitate collected by filtration
  7. customPurification
  8. customwas carried out by recrystallisation from EtOAc/MeOH

Sources & evidence

ORD record
ord-3229222e1b8f4d2fbb784071b3ea134e
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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