Thioacetamide → HCID 66846922, compound

HRID 1466681Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH:5](Br)[C:6]([C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])=O)[CH3:2].[C:19]([NH2:22])(=[S:21])[CH3:20]>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:6]2[N:22]=[C:19]([CH3:20])[S:21][C:5]=2[C:4]([O:3][CH2:1][CH3:2])=[O:18])[CH:13]=1

Participants

Reactant 2

HCID 2723949Thioacetamide

HCID 86668389HCID 86668389, compound

Product 1

HCID 66846922HCID 66846922, compound

Procedure

Using 2-bromo-3-(5-chloro-2-methoxy-phenyl)-3-oxo-propionic acid ethyl ester and thioacetamide, the title compound was prepared following the synthetic procedures described for ethyl 2-amino-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate with additional purification by flash chromatography on silica gel (50 to 100% DCM in cyclohexane) to give ethyl 4-(5-chloro-2-methoxyphenyl)-2-methylthiazole-5-carboxylate. LCMS (ESI) m+H=321.4; 1H NMR (400 MHz, CDCl3): δ 7.38 (d, 1H); 7.33 (dd, 1H); 6.87 (d, 1H); 4.20 (q, 2H); 3.75 (s, 3H); 2.76 (s, 3H); 1.20 (t, 3H).

Workup

customthe title compound was prepared
customdescribed for ethyl 2-amino-4-(5-chloro-2-methoxyphenyl)thiazole-5-carboxylate with additional purification by flash chromatography on silica gel (50 to 100% DCM in cyclohexane)

Sources & evidence

ORD record: ord-f80eb30f99a3411f843d16e02b15bfa1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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