5-Bromo-2-chloropyrimidine → HCID 22282015, compound

HRID 1368582Notes

Reaction equation

HRID 1368582 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:22][C:23]2[N:27]([CH3:28])[N:26]=[C:25]([O:29][CH2:30][CH2:31][OH:32])[C:24]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([CH3:12])([CH3:11])[CH3:10]>>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:32][CH2:31][CH2:30][O:29][C:25]2[C:24]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[C:23]([NH:22][S:19]([C:16]3[CH:17]=[CH:18][C:13]([C:9]([CH3:11])([CH3:10])[CH3:12])=[CH:14][CH:15]=3)(=[O:20])=[O:21])[N:27]([CH3:28])[N:26]=2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 22281897HCID 22281897, compound

Product 1

HCID 22282015HCID 22282015, compound

Procedure

The title compound was made according to the procedure used for Example 13 except that (63 mg) of 5-bromo-2-chloropyrimidine was used and that 4-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1-methyl-4-phenyl-1H-pyrazol-5-yl}benzenesulfonamide (Example 15) (80 mg) was used in place of 4-(tert-butyl)-N-{3-(2-hydroxyethoxy)-1-methyl-4-[4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}benzenesulfonamide (Example 12). The crude material was purified by HPLC on a 5μ ODS Phenomenex Magellen™ column with a gradient elution of acetonitrile (5% to 95%) and 0.1M NH4OAc (95% to 5%) to yield the desired product as an off white solid (52 mg).

Workup

  1. customThe crude material was purified by HPLC on a 5μ ODS Phenomenex Magellen™ column with a gradient elution of acetonitrile (5% to 95%) and 0.1M NH4OAc (95% to 5%)

Sources & evidence

ORD record
ord-3c3e852f2f8943c68be88063d7da39c9
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

Loading…