Sodium Hydroxide → 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917720Notes

Reaction equation

HRID 917720 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:3]=1[NH:4][C:5]1[C:6]([C:21]([O:23]CC)=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:9](=[O:11])[CH:10]=1.[OH-].[Na+]>CCO>[F:1][C:2]1[CH:29]=[C:28]([I:30])[CH:27]=[CH:26][C:3]=1[NH:4][C:5]1[C:6]([C:21]([OH:23])=[O:22])=[CH:7][N:8]([CH2:12][CH2:13][O:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[C:9](=[O:11])[CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 23630801Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 589628554-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylic acidYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylate was dissolved in EtOH and treated with 1 M NaOH, as for example 1, step C, to hydrolyse the ester to give 4-(2-fluoro-4-iodoanilino)-6-oxo-1-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-1,6-dihydro-3-pyridinecarboxylic acid as a pale yellow solid (88%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 13.33 (v br s, 1H), 9.67 (br s, 1H), 8.46 (s, 1H), 7.77 (dd, J=10.0, 1.8 Hz, 1H), 7.60 (dd, J=8.3, 0.9 Hz, 1H), 7.32 (t, J=8.5 Hz, 1H), 5.50 (s, 1H), 4.60-4.56 (m, 1H), 4.12-4.06 (m, 2H), 3.79-3.71 (m, 1H), 3.60-3.35 (m, 3H), 1.75-1.27 (m, 6H). LCMS (APCI−) calcd for C19H19FIN2O5 501 (MH+), found 501.

Sources & evidence

ORD record
ord-4cdf595f69dd43fca003e483e2ff253d
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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