Pyridine → HCID 66847113, compound

HRID 1466674Notes

Reaction equation

[NH2:1][C:2](=O)[CH:3]([NH:13][C:14](=O)[CH2:15][C:16](O)([CH3:18])[CH3:17])[C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[O:11][CH3:12].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:10][C:8]1[CH:7]=[CH:6][C:5]([O:11][CH3:12])=[C:4]([C:3]2[N:13]=[C:14]([CH:15]=[C:16]([CH3:18])[CH3:17])[S:31][C:2]=2[NH2:1])[CH:9]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-(2-amino-1-(5-chloro-2-methoxyphenyl)-2-oxoethyl)-3-hydroxy-3-methylbutanamide (240 mg, 0.762 mmol), Lawesson's reagent (308 mg, 0.76 mmol) and pyridine (2.5 mL) was heated to 100° C. for 18 hours. After cooling, DCM was added and the mixture washed with water, sodium hydrogen carbamate (sat. aq.) and brine, and concentrated to dryness. 4-(5-chloro-2-methoxyphenyl)-2-(2-methylprop-1-enyl)thiazol-5-amine (51.0 mg) was isolated as a pale yellow solid. LCMS (ESI) m+H=295.3; NMR (400 MHz, DMSO-d6): δ 7.38 (d, 1H); 7.31 (dd, 1H); 7.09 (d, 1H); 6.24 (t, 1H); 5.50 (s, br, 2H); 3.83 (s, 3H); 2.02 (d, 3H); 1.89 (s, 3H).

Workup

temperatureAfter cooling
washthe mixture washed with water, sodium hydrogen carbamate (sat. aq.) and brine
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-804f824b665e49bf90b33ec5e7472b31
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999998B2

Reaction notes

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