3-Amino-1-propanol → 4-(2-fluoro-4-iodoanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide

HRID 917701Notes

Reaction equation

HRID 917701 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.[NH2:32][CH2:33][CH2:34][CH2:35][OH:36].CCN(C(C)C)C(C)C>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:32][CH2:33][CH2:34][CH2:35][OH:36])=[O:20])=[CH:12][N:13]([CH3:31])[C:14](=[O:30])[CH:15]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 865963782,3,4,5,6-Pentafluorophenyl-4-(2-fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 111667134-(2-fluoro-4-iodoanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamideYield 95%

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 was reacted with 3-aminopropanol in THF in the presence of DIEA as for example 4, step B. The reaction solvent was removed under reduced pressure and the resulting oil purified by chromatography on silica gel (50% acetone/CH2Cl2) to give 4-(2-fluoro-4-iodoanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide as a white solid (95%), m.p. (Et2O) 81-86° C. 1H NMR [(CD3)2SO, 400 MHz] δ 10.11 (s, 1H), 8.40 (br s, 1H), 8.24 (s, 1H), 7.74 (d, J=9.7 Hz, 1H), 7.58 (d, J=8.2 Hz, 1H), 7.29 (t, J=8.5 Hz, 1H), 5.59 (s, 1H), 4.48 (t, J=5.1 Hz, 1H), 3.48 (q, J=5.7 Hz, 2H), 3.37 (s, 3H), 3.30-3.24 (m, 2H), 1.67 (pentet, J=6.7 Hz, 2H). Anal. Calcd for C16H17FIN3O3.0.5H2O: C, 42.3; H, 4.0; N, 9.3. Found: C, 42.2; H, 3.8; N, 9.1.

Workup

  1. customThe reaction solvent was removed under reduced pressure
  2. customthe resulting oil purified by chromatography on silica gel (50% acetone/CH2Cl2)

Sources & evidence

ORD record
ord-f004c04d4e254b5da5dba805948f2044
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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