Morpholine → HCID 68359256, compound

HRID 339911Notes

Reaction equation

HRID 339911 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18](O)=[O:19])=[CH:13][CH:12]=1)(=[O:9])=[O:8].C(N(CC)CC)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:1][O:2][C:3]1[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:4]=1[CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:19])=[CH:13][CH:12]=1)(=[O:8])=[O:9]

Participants

7

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68291902HCID 68291902, compound

Product 1

HCID 68359256HCID 68359256, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of {4-[(2,4-dimethoxybenzylsulfamoyl)methyl]phenyl}acetic acid (356 mg) in DMF (15 ml) were added triethylamine (237 mg), morpholine (97 mg) and HATU (392 mg). The mixture was stirred at room temperature for 17 h, then added to water (200 ml) and extracted with ethyl acetate. After washing with water, 1 M hydrochloric acid, sodium hydrogencarbonate solution and sodium chloride solution, the organic phase was dried over magnesium sulfate and concentrated. This gave the product (313 mg) with a molecular weight of 448.5 g/mol (C22H28N2O6S).

Workup

  1. extractionextracted with ethyl acetate
  2. washAfter washing with water, 1 M hydrochloric acid, sodium hydrogencarbonate solution and sodium chloride solution
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-63d4e85cf4ee4ce4840ff0608afae18d
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

Loading…