5-Bromo-2-chloropyrimidine → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-4-(tert-butyl)benzenesulfonamide

HRID 1368583Notes

Reaction equation

HRID 1368583 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3[C:19]([O:38][CH2:39][CH2:40][OH:41])=[N:20][N:21]([CH3:37])[C:22]=3[NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:17][C:12]=2[O:11][CH2:10]1>>[O:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]3[C:19]([O:38][CH2:39][CH2:40][O:41][C:5]4[N:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=4)=[N:20][N:21]([CH3:37])[C:22]=3[NH:23][S:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:34])[CH3:35])=[CH:29][CH:28]=3)(=[O:26])=[O:25])=[CH:17][C:12]=2[O:11][CH2:10]1

Participants

3

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 22282036N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide

Product 1

HCID 9960849N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-bromo-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-4-(tert-butyl)benzenesulfonamide

Procedure

The title compound was made according to the procedure used for Example 13 except that (45 mg) of 5-bromo-2-chloropyrimidine was used and that N-[4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-4-(tert-butyl)benzenesulfonamide (Example 17) (70 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 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 (19.6 mg).

Workup

  1. customThe crude 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-2c1ee1a6f3204e73b7459fb9bc78cce0
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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