N'-tert-butylpropane-1,3-diamine

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7.0 g (23 mmol) of ethyl 4,5-diphenyl-1H-imidazole-1-acetate of example 1 and 4.5 g (34.6 mmol) of 3-(t-butylamino)propylamine, conveniently made by LAH reduction of 3-(t-butylamino)propionitrile in THF, was heated at 100° C. for 8 hr. The residue was distributed between water and methylene chloride, and the methylene chloride layer was dried over MgSO4 and stripped. The residue was recrystallized from ether and then cyclohexane to yield 4.5 g of product, mp 94°-96° C. the methylene chloride layer was dried over MgSO4 The residue was recrystallized from ether

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 7.0 g (23 mmol) of ethyl 4,5-diphenyl-1H-imidazole-1-acetate of example 1 and 4.5 g (34.6 mmol) of 3-(t-butylamino)propylamine, conveniently made by LAH reduction of 3-(t-butylamino)propionitrile in THF, was heated at 100° C. for 8 hr. The residue was distributed between water and methylene chloride, and the methylene chloride layer was dried over MgSO4 and stripped. The residue was recrystallized from ether and then cyclohexane to yield 4.5 g of product, mp 94°-96° C. the methylene chloride layer was dried over MgSO4 The residue was recrystallized from ether

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

Procedure: In a manner analogous to that of Example 1, 400 ml of triethylamine are added to 317 g (2.2 mols) of maleic acidmonoethyl ester, and the mixture is subsequently reacted with 260 g (2.0 mols) of 3-tert-butylaminopropylamine. The reaction mixture is further processed as in Example 1 to yield 423.4 g (77.2% of theory) of a white crystalline aspartic acid derivative, which melts at 174°-175° C. after recrystallisation in a mixture of ethanol/acetone (1:3).

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

Procedure: In a manner analogous to that of Example 1, 400 ml of triethylamine are added to 317 g (2.2 mols) of maleic acidmonoethyl ester, and the mixture is subsequently reacted with 260 g (2.0 mols) of 3-tert-butylaminopropylamine. The reaction mixture is further processed as in Example 1 to yield 423.4 g (77.2% of theory) of a white crystalline aspartic acid derivative, which melts at 174°-175° C. after recrystallisation in a mixture of ethanol/acetone (1:3).

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

Procedure: The title compound was prepared from 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide and N-(1,1-dimethylethyl)-1,3-propanediamine by following the procedures in Example 79c. LC-MS m/z 604 (M+H)+; 1H-NMR (MeOD) 1.09 (m, 9H), 1.70 (m, 2H), 2.33 (m, 3H), 2.47 (m, 1H), 2.66 (m, 1H), 3.13 (m, 1H), 3.47 (m, 1H), 6.36 (d, J=8.8 Hz, 1H), 7.10 (m, 1H), 7.23 (m, 2H), 7.47 (m, 2H), 7.58 (m, 2H), 8.04 (m, 1H), 8.13 (d, J=7.6 Hz, 1H).

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

Procedure: The title compound was prepared from 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide and N-(1,1-dimethylethyl)-1,3-propanediamine by following the procedures in Example 79c. LC-MS m/z 604 (M+H)+; 1H-NMR (MeOD) 1.09 (m, 9H), 1.70 (m, 2H), 2.33 (m, 3H), 2.47 (m, 1H), 2.66 (m, 1H), 3.13 (m, 1H), 3.47 (m, 1H), 6.36 (d, J=8.8 Hz, 1H), 7.10 (m, 1H), 7.23 (m, 2H), 7.47 (m, 2H), 7.58 (m, 2H), 8.04 (m, 1H), 8.13 (d, J=7.6 Hz, 1H).

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 title compound was prepared from 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide and N-(1,1-dimethylethyl)-1,3-propanediamine by following the procedures in Example 79c. LC-MS m/z 604 (M+H)+; 1H-NMR (MeOD) 1.09 (m, 9 H), 1.70 (m, 2 H), 2.33 (m, 3 H), 2.47 (m, 1 H), 2.66 (m, 1 H), 3.13 (m, 1 H), 3.47 (m, 1 H), 6.36 (d, J=8.8 Hz, 1 H), 7.10 (m, 1 H), 7.23 (m, 2 H), 7.47 (m, 2 H), 7.58 (m, 2 H), 8.04 (m, 1 H), 8.13 (d, J=7.6 Hz, 1 H).

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

Procedure: The title compound was prepared from 3-[8-(2,6-difluorophenyl)-2-(methylsulfinyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-4-yl]-4-methyl-N-1,3-thiazol-2-ylbenzamide and N-(1,1-dimethylethyl)-1,3-propanediamine by following the procedures in Example 79c. LC-MS m/z 604 (M+H)+; 1H-NMR (MeOD) 1.09 (m, 9 H), 1.70 (m, 2 H), 2.33 (m, 3 H), 2.47 (m, 1 H), 2.66 (m, 1 H), 3.13 (m, 1 H), 3.47 (m, 1 H), 6.36 (d, J=8.8 Hz, 1 H), 7.10 (m, 1 H), 7.23 (m, 2 H), 7.47 (m, 2 H), 7.58 (m, 2 H), 8.04 (m, 1 H), 8.13 (d, J=7.6 Hz, 1 H).