2-amino-1,3-thiazol-4-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The similar procedure as described in example 35 was used, starting from 4-(6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester, 2-Amino-thiazol-4-one (example 48b), sodium acetate and acetic acid to obtain 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. Purification was performed with flash chromatography (Merck silica gel 60, 230-400 mesh, 1%-5% methanol in dichloromethane for 30 min. LC-MS m/e 455.5 (MH+).

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

Procedure: Similar procedure as described in example 34 was used, starting with 4-ethoxy-quinoline-6-carbaldehyde (example 3b), 2-amino-thiazol-4-one, sodium acetate and acetic acid to give 2-Amino-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 300 (MH+).

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4-[2-Fluoro-4-(2-imino-4-oxo-thiazolidin-5-ylidenemethyl)-phenoxy]-naphthalene-1-carbonitrile was prepared using 2-amino-thiazol-4-one and 4-(2-Fluoro-4-formyl-phenoxy)-naphthalene-1-carbonitrile following General Procedure C. 1H NMR (400 MHz, DMSO-d6) δ 9.54 (br, 1H), 9.25 (br, 1H), 8.42 (d, J=8.21 Hz, 1H), 8.15 (d, J=8.21 Hz, 1H), 8.08 (d, J=7.82 Hz, 1H), 7.91 (m, 1H), 7.81 (m, 1H), 7.7 (dd, J=12.13 and 2.34 Hz, 1H), 7.64 (s, 1H), 7.49-7.57 (2H), 6.93 (d, J=7.83 Hz, 1H). LC/MS (m/z) [M+1]+390.2 (calculated for C21H13FN3O2S 390.1).

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

Procedure: 4-[2-Chloro-4-(2-imino-4-oxo-thiazolidin-5-ylidenemethyl)-phenoxy]-3-trifluoromethyl-benzonitrile was prepared using 2-amino-thiazol-4-one and 4-[2-Chloro-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-phenoxy]-3-trifluoromethylbenzonitrile according to General Procedure C. 1H NMR (400 MHz, DMSO-d6) δ 9.56 (br, 1H), 9.24 (br, 1H), 8.40 (d, J=1.56 Hz, 1H), 8.08 (dd, J=8.6 and 1.95 Hz, 1H), 7.90 (d, J=1.96 Hz, 1H), 7.65 (d, J=2.35 Hz, 1H), 7.63 (s, 1H), 7.50 (d, J=8.61 Hz, 1H), 7.07 (d, J=8.61 Hz, 1H). LC/MS (m/z) [M+1]+424.2 (calculated for C18H10ClF3N3O2S 424.0).

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

Procedure: 4-[4-(2-Amino-4-oxo-4H-thiazol-5-ylidenemethyl)-2-methoxy-phenoxy]-3-chloro-benzonitrile was prepared using 2-amino-thiazol-4-one and 4-(2-Chloro-4-cyanophenoxy)-3-methoxybenzaldehyde according to General Procedure B. 1H NMR (400 Hz, DMSO-d6) δ 9.47 (bs, NH), 9.21 (bs, NH), 8.17 (d, 1H), 7.70 (dd, 1H), 7.64 (s, 1H), 7.46 (d, 1H), 7.32 (d, 1H), 7.23 (dd, 1H), 6.81 (d, 1H), 3.79 (s, 3H); LC/MS (m/z) [M+1]+386.0 (calculated for C18H13ClN3O3S, 386.82).

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

Procedure: 4-[4-(2-Amino-4-oxo-4H-thiazol-5-ylidenemethyl)-2-methoxy-phenoxy]-3-trifluoromethyl-benzonitrile was prepared using 2-amino-thiazol-4-one and 4-(4-Formyl-2-methoxy-phenoxy)-3-trifluoromethyl-benzonitrile according to General Procedure B. 1H NMR (400 Hz, DMSO-d6) δ 8.96 (bs, NH), 8.74 (bs, NH), 8.32 (d, 1H), 7.99 (dd, 1H), 7.65 (d, 1H), 7.47 (d, 1H), 7.36 (d, 1H), 7.24 (d, 1H), 6.89 (d, 1H), 3.88 (s, 3H); LC/MS (m/z) [M+1]+420.0 (C19H13F3N3O3S, 420.38).

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

Procedure: The similar procedure as described in example 35 was used, starting from 4-(6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester, 2-Amino-thiazol-4-one (example 48b), sodium acetate and acetic acid to obtain 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. Purification was performed with flash chromatography (Merck silica gel 60, 230-400 mesh, 1%-5% methanol in dichloromethane for 30 min. LC-MS m/e 455.5 (MH+).

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

Procedure: Similar procedure as described in example 34 was used, starting with 4-ethoxy-quinoline-6-carbaldehyde (example 3b), 2-amino-thiazol-4-one, sodium acetate and acetic acid to give 2-Amino-5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 300 (MH+).