Dimethylformamide → HCID 54296359, compound

HRID 2085369Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4](/[CH:7]=[CH:8]/[C:9]2[O:10][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:12][N:13]=2)=[CH:5][N:6]=1.CN(C=O)C.C(N(CC)C(C)C)(C)C.[C:32]1([CH2:38][C:39](Cl)=[O:40])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[C:14]([C:11]1[O:10][C:9]([CH:8]=[CH:7][C:4]2[S:3][C:2]([NH:1][C:39](=[O:40])[CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:6][CH:5]=2)=[N:13][CH:12]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-amino-5-[(E)-2-(5-t-butyl-oxazol-2-yl)-vinyl]-thiazole (20 mg, 0.08 mmol) in dry CH2Cl2 (1 mL) was added dry DMF (0.1 mL) and N,N-diisopropylethylamine (28 μL, 0.16 mmol). The resulting solution was cooled to 0° C. and phenyl acetyl chloride (21 μL, 0.16 mmol) was added via syringe. The reaction mixture was allowed to warm to room temperature over two hours and then concentrated. Chromatography (SiO2, 5% MeOH/CH2Cl2) provided a N-[5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]-phenylacetamide as a mixture of Z and E isomers which were separated by reverse-phase HPLC to give the Z isomer (3 mg, 10%, MS m/e 368 (M+H)+) as a light yellow solid, and the E isomer (3 mg, 10%, C20H21N3O2S, MS m/e 368 (M+H)+) as a yellow solid. (Z)-isomer: HPLC-HI 86% at 4.05 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 254 nm). (E)-isomer: HPLC-HI 84% at 4.18 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 254 nm).

Workup

temperatureto warm to room temperature over two hours
concentrationconcentrated

Sources & evidence

ORD record: ord-9ab2999e920d4de0ae4717773579be10
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720347B2

Reaction notes

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