Bromine → HCID 24886276, compound

HRID 268585Notes

Reaction equation

HRID 268585 reaction equation
[Br:1]Br.[CH3:3][N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22](=[O:29])(=[O:28])[NH:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:30].C(=O)([O-])O.[Na+]>C(O)(=O)C.O>[Br:1][C:7]1[N:6]=[C:5]([CH3:30])[N:4]([CH3:3])[C:8]=1[C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:22](=[O:29])(=[O:28])[NH:23][CH2:24][CH2:25][O:26][CH3:27])=[CH:20][CH:21]=2)[N:10]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 22273524HCID 22273524, compound

Product 1

HCID 24886276HCID 24886276, compoundYield 24%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A 1M solution of bromine in acetic acid (8.49 ml, 8.49 mmol) was added to a solution of 4(1,2-dimethylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Example 35 in WO 02/20512; 3.1g, 7.71mmol) in acetic acid (24 ml) heated at 70° C. under nitrogen. The mixture was stirred at 70° C. for 1 hour, allowed to cool, diluted with water and carefully neutralised with saturated aqueous sodium hydrogen carbonate solution. The aqueous solution was extracted with EtOAc, the extracts combined, dried and the volatiles removed by evaporation. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10) to give the title compound (1 g, 24%). NMR: 2.38 (s, 3H), 2.87 (s, 2H), 2.51 (q, 2H), 3.16 (s, 3H), 3.52 (s, 3H), 7.49 (s, 1H), 7.70 (d, 2H), 7.88 (d, 2H), 8.82 (s, 1H).

Workup

  1. temperatureto cool
  2. extractionThe aqueous solution was extracted with EtOAc
  3. customdried
  4. customthe volatiles removed by evaporation
  5. customThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (95:5 increasing in polarity to 90:10)

Sources & evidence

ORD record
ord-92b4977a934c40c6b59a7dde7288c081
Source dataset
uspto-grants-2008_11
Patent number
US07446105B2

Reaction notes

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