Ethanolamine → HCID 11189634, compound

HRID 917700Notes

Reaction equation

HRID 917700 reaction equation
FC1C(F)=C(F)C(F)=C(F)C=1[C:12]1[N:13]([CH3:31])[C:14](=[O:30])[CH:15]=[C:16]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([I:28])=[CH:24][C:23]=2[F:29])[C:17]=1[C:18]([O-:20])=O.CCN(C(C)C)C(C)C.[NH2:41][CH2:42][CH2:43][OH:44]>C1COCC1>[F:29][C:23]1[CH:24]=[C:25]([I:28])[CH:26]=[CH:27][C:22]=1[NH:21][C:16]1[C:17]([C:18]([NH:41][CH2:42][CH2:43][OH:44])=[O:20])=[CH:12][N:13]([CH3:31])[C:14](=[O:30])[CH:15]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 865963782,3,4,5,6-Pentafluorophenyl-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 11189634HCID 11189634, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,3,4,5,6-Pentafluorophenyl-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (600 mg, 1.08 mmol) was dissolved in THF (15 mL) to which was added DIEA (697 mg, 5.40 mmol), followed by 2-aminoethanol (132 mg, 2.17 mmol). This mixture was stirred at R.T. for 2 h., then the reaction solvent removed under reduced pressure and the resulting white solid suspended in Et2O. The solid was collected by filtration, then recrystallised from EtOAc/MeOH to give 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (394 mg, 85%) as a white solid, m.p. (EtOAc/MeOH) 205-208° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.10 (s, 1H), 8.43 (br s, 1H), 8.28 (s, 1H), 7.72 (dd, J=10.2, 1.8 Hz, 1H), 7.56 (br d, J=8.5 Hz, 1H), 7.28 (t, J=8.5 Hz, 1H), 5.58 (s, 1H), 4.76 (br t, J=5.2 Hz, 1H), 3.50 (q, J=5.8 Hz, 2H), 3.36 (s, 3H), 3.32-3.26 (m, 2H). Anal. Calcd for C15H15FIN3O3: C, 41.8; H, 3.5; N, 9.8. Found: C, 4.19; H, 3.2; N, 9.7.

Workup

  1. customthe reaction solvent removed under reduced pressure
  2. filtrationThe solid was collected by filtration
  3. customrecrystallised from EtOAc/MeOH

Sources & evidence

ORD record
ord-de000bb5957d484e8c651f3e231d142b
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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