2-Chloro-1,4-diiodobenzene

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 95-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 95-B ethylmagnesium bromide was used in place of methylmagnesium chloride; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 95-F was omitted, and (iv) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described in steps 33-T and 33-U) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 95-G. HR-MS: calcd for C31H30ClIN4O5 [M+H+] 701.1022. Found 701.1017. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 95-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 95-B ethylmagnesium bromide was used in place of methylmagnesium chloride; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 95-F was omitted, and (iv) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described in steps 33-T and 33-U) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 95-G. HR-MS: calcd for C31H30ClIN4O5 [M+H+] 701.1022. Found 701.1017. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 94-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 93-B ethylmagnesium bromide was used in place of methylmagnesium chloride and (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 94-F was omitted. HR-MS: calcd for C30H28ClIN4O4 [M+H+] 671.0917. Found 671.0917. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 82-A step 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 82-E (S)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid, and (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 82-F was omitted. HR-MS: calcd for C25H26ClIN4O4 [M+H+] 609.0760. Found 609.0757. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 82-A step 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 82-E (S)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid, and (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 82-F was omitted. HR-MS: calcd for C25H26ClIN4O4 [M+H+] 609.0760. Found 609.0757. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 35-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step F was omitted; and (iii) cyclization of (R)-2-amino-N-{(1S,2S)-1-[5-(2-chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2-[4-(2-hydroxy-ethoxy)-phenyl]-acetamide in step 35-H was performed as described in example 34. HR-MS: calcd for C29H26ClIN4O4 [M+H+] 657.07600. Found 657.0757. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 95-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 95-B ethylmagnesium bromide was used in place of methylmagnesium chloride; (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 95-F was omitted, and (iv) (R)-tert-butoxycarbonylamino-[4-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-acetic acid (prepared as described in steps 33-T and 33-U) was used in place of (R)-tert-butoxycarbonylamino-[4-(2-tert-butoxy-ethoxy)-phenyl]-acetic acid in step 95-G. HR-MS: calcd for C31H30ClIN4O5 [M+H+] 701.1022. Found 701.1017. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 94-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 93-B ethylmagnesium bromide was used in place of methylmagnesium chloride and (iii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 94-F was omitted. HR-MS: calcd for C30H28ClIN4O4 [M+H+] 671.0917. Found 671.0917. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 82-A step 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) in step 82-E (S)-2-tert-butoxycarbonylamino-4-methyl-pentanoic acid was used in place of (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-butyric acid, and (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step 82-F was omitted. HR-MS: calcd for C25H26ClIN4O4 [M+H+] 609.0760. Found 609.0757. Prepared by the same method

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

Procedure: Prepared by the same method as described in example 1 except that (i) in step 35-A 2-chloro-1,4-diiodo-benzene was used in place of 2-fluoro-1,4-diiodo-benzene; (ii) chlorination of the 5-position of the imidazole ring with N-chlorosuccinimide in step F was omitted; and (iii) cyclization of (R)-2-amino-N-{(1S,2S)-1-[5-(2-chloro-4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2-[4-(2-hydroxy-ethoxy)-phenyl]-acetamide in step 35-H was performed as described in example 34. HR-MS: calcd for C29H26ClIN4O4 [M+H+] 657.07600. Found 657.0757. Prepared by the same method