Methylamine → 2-(3-Methyl-ureido)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 239103Notes

Reaction equation

HRID 239103 reaction equation
[CH3:1][NH2:2].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]=[C:17]([NH:19][C:20]([O:22]C3C=CC=CC=3)=O)[S:18][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C.O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C:13]2[N:16]=[C:17]([NH:19][C:20]([NH:2][CH3:1])=[O:22])[S:18][C:12]=2[CH2:11]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 866860322-Phenoxycarbonylamino-6,7-dihydro-4H-thiazolo(5,4-c)pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 584408222-(3-Methyl-ureido)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl esterYield 90.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

25 mg methylamine 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 151 mg of desired product. (M+H)+: 313

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-2185d9e6a0074cbcbc33185c38921d33
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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