Diethylethanolamine → HCID 58879980, compound

HRID 1361419Notes

Reaction equation

HRID 1361419 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][C:12]=2[F:20])[CH:7]=[CH:6][N:5]=1)(=[O:3])[NH2:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:45][C:46]1[C:47](=[O:59])[N:48]([C:52]2[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=2)[CH:49]=[CH:50][CH:51]=1.CCN(CCO)CC>CN(C=O)C.CO>[F:20][C:12]1[CH:13]=[C:14]([C:15](=[O:17])[NH:45][C:46]2[C:47](=[O:59])[N:48]([C:52]3[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=3)[CH:49]=[CH:50][CH:51]=2)[CH:18]=[CH:19][C:11]=1[O:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([C:1]([NH2:2])=[O:3])[CH:9]=1

Participants

7

Reactant 4

HCID 7497DiethylethanolamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58879956HCID 58879956, compoundHCID 588799723-amino-1-(4-fluorophenyl)pyridin-2(1H)-one

Product 1

HCID 58879980HCID 58879980, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(2-carbamoylpyridin-4-yloxy)-3-fluorobenzoic acid (0.3 mmol, 83 mg) in DMF (2 mL), were added HATU (Perspective Biosystems, 0.45 mmol, 171 mg), 3-amino-1-(4-fluorophenyl)pyridin-2(1H)-one (0.3 mmol, 61.2 mg) and DEEA (Aldrich, 0.2 mL). The reaction mixture were heated at 50° C. for 5 h. After cooling to room temperature, 5 mL of methanol was added. The product was purified by preparative HPLC. The desired fractions were combined, neutralized to pH 7-8 with aq. K2HPO4, and concentrated in vacuo. The precipitate that formed was collected by filtration, rinsed with water, and dried under vacuum to give the desired product (78 mg, 57% yield). MS(ESf+) m/z 463.25 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe product was purified by preparative HPLC
  3. concentrationconcentrated in vacuo
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. washrinsed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ecdfdf6fdb3e451dbf7821a3bb60bcd1
Source dataset
uspto-grants-2011_02
Patent number
US07880004B2

Reaction notes

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