Methylamine → HCID 70098016, compound
Reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:11][C:10]=1[C:20]([OH:22])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.CN>C1COCC1>[CH3:23][NH:24][C:20]([C:10]1[N:11]=[C:12]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:13][C:9]=1[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
A solution of 5-tert-butoxycarbonylamino-2-phenyl-thiazole-4-carboxylic acid (138 mg, 0.43 mmol) in THF (2.5 ml) was treated with HATU (187 mg, 0.49 mmol), N-methylmorpholin (0.25 ml, 2.24 mmol) and methylamine (0.29 ml, 2M THF solution) and stirred at 75° C. for 6 h. The reaction mixture was partitioned between potassium hydrogen sulfate (10% aqueous solution) and ethyl acetate and extracted. The organic layer was washed with water, sodium bicarbonate and brine. The combined organic phases were dried and the solvent was evaporated. The product was obtained after purification by silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (98 mg, 65%).
Workup
- customThe reaction mixture was partitioned between potassium hydrogen sulfate (10% aqueous solution) and ethyl acetate
- extractionextracted
- washThe organic layer was washed with water, sodium bicarbonate and brine
- customThe combined organic phases were dried
- customthe solvent was evaporated
- customThe product was obtained
- customafter purification by silica gel chromatography
Sources & evidence
- ORD record
- ord-1debe5be01414315a78890b22f9c0d75
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703768B2
Reaction notes
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