3-Methoxypropionic acid → HCID 22479010, compound

HRID 2090263Notes

Reaction equation

HRID 2090263 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[CH:14][C:13]=1[NH2:22])([CH3:4])([CH3:3])[CH3:2].[CH3:24][O:25][CH2:26][CH2:27][C:28](O)=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN1C(=O)CCC1.C(OCC)C.CCOC(C)=O>[CH3:24][O:25][CH2:26][CH2:27][C:28]1[N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:23])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:22]=1

Participants

7

Reactant 3

HCID 1344423-Methoxypropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66958404HCID 66958404, compound

Product 1

HCID 22479010HCID 22479010, compoundYield 151.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

To the product of example 1 step (iii) (1.9 g) in NMP (25 mL), 3-methoxypropanoic acid (0.678 mL, 7.21 mmol) was added followed by HATU (2.74 g) and TEA (0.837 mL) under nitrogen. The resulting solution was stirred at 60° C. for 15 h. The reaction mixture was diluted with diethyl ether (300 mL) and EtOAc (300 mL), and washed with water (300 mL), sat. NaHCO3 (200 mL), and saturated brine (200 mL). The organic was dried, filtered and evaporated to afford the subtitle product (3.5 g).

Workup

  1. washwashed with water (300 mL), sat. NaHCO3 (200 mL), and saturated brine (200 mL)
  2. customThe organic was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-11f1c312654a4379b2c92488f476ab86
Source dataset
uspto-grants-2013_05
Patent number
US08436178B2

Reaction notes

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