2-(4-chlorophenyl)acetohydrazide

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in analogy to example 71c) starting with [3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-thiourea (150 mg, 0.57 mmol) and (4-chloro-phenyl)-acetic acid hydrazide (116 mg, 0.57 mmol). Obtained as a brownish solid (36 mg, 16%) after chromatography of the crude reaction product on amino-modified silica gel (Merck HPTLC Silica Gel 60 NH2F254S) using ethyl acetate as eluent.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A stirred solution of 7.0 grams (0.038 mole) of 4-chlorophenylacetic acid hydrazide, 3.0 grams (0.039 mole) of carbon disulfide and 2.8 grams (0.050 mole) of potassium hydroxide in 10 ml of water and 200 ml of ethanol was heated under reflux for four hours. The ethanol was removed under reduced pressure. The concentrate was taken up in water and the mixture washed with diethyl ether. The aqueous layer was acidified with aqueous 5% hydrochloric acid and then was extracted with diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 3.9 grams of 2-(4-chlorophenylmethyl)-5-mercapto-1,3,4-oxadiazole; m.p. 115° C. The nmr spectrum was consistent with the proposed structure. under reflux for four hours The ethanol was removed under reduced pressure the mixture washed with diethyl ether was extracted with diethyl ether The extract was dried with magnesium sulfate filtered The filtrate was concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared in a similar manner to that described in example 3 from 5-(1,1-dioxido-1,2-thiazinan-2-yl)-8-hydroxy-1,6-naphthyridine-7-carbonitrile (75 mg, 0.24 mmol) and 2-(4-chlorophenyl)acetic hydrazide (137 mg, 0.74 mmol) to give a white solid (49 mg, 43%). 1H NMR (CDCl3/CD3OD): δ 9.06 (d, J=3.6 Hz, 1 H), 8.62 (d, J=8.4 Hz, 1 H), 7.66 (dd, J=8.4, 4.0 Hz, 1 H), 7.28-7.21 (m, 4 H), 4.15 (s, 2 H), 3.89 (m, 1 H), 3.82 (m, 1 H), 3.63 (m, 1 H), 3.31 (m, 1 H), 2.41 (m, 3 H), 1.79 (m, 1 H); MS m/z 471 (M+1).