Allylamine → 2-(3-allyl-ureido)-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

HRID 400428Notes

Reaction equation

HRID 400428 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2[N:18]=[C:19]([NH:21][C:22]([O:24]C3C=CC=CC=3)=O)[S:20][C:14]=2[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C.O>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2[N:18]=[C:19]([NH:21][C:22]([NH:4][CH2:1][CH:2]=[CH2:3])=[O:24])[S:20][C:14]=2[CH2:13]1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

5

Reactant 2

HCID 7853AllylamineHCID 866860322-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 866860332-(3-allyl-ureido)-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl esterYield 99.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

45 mg allylamin was added to 200 mg 2-phenoxycarbonylamino-6,7-dihydro-4H-thiazolo (5,4-c) pyridine-5-carboxylic acid tert-butyl ester in 25 mL DMF. The reaction was stirred for 12 h at RT, diluted with water and extracted with ethyl acetate. The organic layer was washed with brine solution and concentrated. The residue was purified by column chromatographie (silica gel, eluent: 40% ethylacetate in hexane) to give 179 mg of desired product. (M+H)+: 339

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine solution
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatographie (silica gel, eluent: 40% ethylacetate in hexane)

Sources & evidence

ORD record
ord-accd5698b32e4e9fbcdad951146c32f6
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

Loading…