Ethyl isocyanate → Methyl 4-(2-(3-ethylureido)thiazol-4-yl)benzoate

HRID 2243022Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=2)[N:6]=1.[CH2:17]([N:19]=[C:20]=[O:21])[CH3:18]>CN1C(=O)CCC1>[CH2:17]([NH:19][C:20]([NH:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:15][CH:16]=2)[N:6]=1)=[O:21])[CH3:18]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of methyl 4-(2-amino-1,3-thiazol-4-yl)benzoate (Intermediate 11; 150 mg, 0.64 mmol) in NMP (3 mL), ethyl isocyanate (90 μl, 1.14 mmol) was added. The solution was heated at 110° C. for one hour in a microwave. The crude was partitioned between water and EtOAc. The organic layer was washed with NaHCO3 solution, water and brine. It was dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography (2% MeOH in DCM) to give the desired product (79 mg). MS (ESP): 306 (M+H+) for C14H15N3O3S; NMR: 1.06 (t, 3H), 3.12-3.16 (m, 2H), 3.85 (s, 3H), 6.48 (s, 1H), 7.66 (s, 1H), 7.98 (s, 4H), 10.65 (s, 1H).

Workup

customThe crude was partitioned between water and EtOAc
washThe organic layer was washed with NaHCO3 solution, water and brine
dry with materialIt was dried over magnesium sulfate
concentrationconcentrated
customThe residue was purified by flash chromatography (2% MeOH in DCM)

Sources & evidence

ORD record: ord-83a2cb0939454a6794d4c443c0b5d39e
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

Loading…