Methylamine → HCID 22593936, compound

HRID 1386009Notes

Reaction equation

HRID 1386009 reaction equation
[S:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][CH:21]([O:25][CH2:26][CH3:27])[C:22](O)=[O:23])=[CH:16][CH:15]=2)[CH2:3][CH2:2]1.[CH2:28]([N:30](CC)CC)C.C(Cl)(=O)C(C)(C)C.CN>ClC.O>[CH3:28][NH:30][C:22](=[O:23])[CH:21]([O:25][CH2:26][CH3:27])[CH2:20][C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][N:4]2[C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[S:1][CH2:2][CH2:3]2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 9909435HCID 9909435, compound

Product 1

HCID 22593936HCID 22593936, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6327Methyl ChlorideSolvent

Procedure

To an ice cooled solution of 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid (0.3 g, 0.78 mmol) obtained in example 29 and triethylamine (0.162 g, 1.6 mmol) in dry chloromethane (10 mL) was added pivaloyl chloride (0.10 g, 0.86 mmol) and stirring was continued for 30 min at 0° C. To the above reaction mixture, methyl amine (40% solution) (0.124 mL) was added at 25° C. and stirring was continued for 1 h at 25° C. Water (20 mL) was added and extracted with ethyl acetate (2×20 mL). The combined organic extract was washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure. The residue was chromatographed over silica gel using a mixture of ethyl acetate and pet. ether (1:1) to afford the title compound as a colorless solid. mp: 80-82° C.

Workup

  1. stirringstirring
  2. waitwas continued for 1 h at 25° C
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. extractionThe combined organic extract
  5. washwas washed with water (10 mL), brine (10 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was chromatographed over silica gel using
  10. additiona mixture of ethyl acetate and pet. ether (1:1)

Sources & evidence

ORD record
ord-2eb8ec4ac4164741b9b0ae89f1426867
Source dataset
uspto-grants-2001_07
Patent number
US06265401B1

Reaction notes

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