Ethanolamine → HCID 58962860, compound

HRID 917790Notes

Reaction equation

HRID 917790 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]([C:18]([OH:20])=O)=[CH:12][N:13]([CH3:17])[C:14](=[O:16])[CH:15]=2)=[C:5]([F:21])[CH:4]=1)[CH3:2].FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O.N1C=CC=CC=1.[NH2:46][CH2:47][CH2:48][OH:49]>CN(C=O)C>[OH:49][CH2:48][CH2:47][NH:46][C:18]([C:11]1[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[F:21])=[CH:15][C:14](=[O:16])[N:13]([CH3:17])[CH:12]=1)=[O:20]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 1049PyridineHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 11392136HCID 11392136, compound

Product 1

HCID 58962860HCID 58962860, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Ethyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (0.50 g, 1.72 mmol) was reacted with pentafluorophenyl trifluoroacetate (0.92 mL, 5.20 mmol) in the presence of pyridine (0.45 mL) in DMF (15 mL). The solution was allowed to stir at room temperature for 15 hours and then treated with 2-Amino-ethanol (0.50 mL, 8.60 mmol) as in example 75 to afford the 4-(4-Ethyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (2-hydroxy-ethyl)-amide (0.47 g, 82%). 1H NMR [400 MHz, (CD3)2SO] δ 9.82 (s, 1H), 8.35 (t, J=5.4 Hz, 1H), 8.20 (s, 1H), 7.27 (t, J=8.4 Hz, 1H), 7.12 (d, J=11.8 Hz, 1H), 7.06 (d, J=7.7 Hz, 1H), 5.38 (s, 1H), 4.72 (t, J=5.1 Hz, 1 H, OH), 3.44 (t, J=11.5, 6.2 Hz, 2H), 3.35 (s, 3H), 3.22 (t, J=12.8, 6.8 Hz, 2H), 2.58 (q, J=7.1 Hz, 2H), 1.14 (t, J=7.1 Hz, 3H). (APCI+) calcd for C17H20FN3O3 333.36 (M+1), found 334.1.

Sources & evidence

ORD record
ord-c9702d1eb1714644bac50fd14fa0931e
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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