Bromine → HCID 22273571, compound

HRID 1064318Notes

Reaction equation

HRID 1064318 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:25])(=[O:24])[NH2:23])=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[CH:5]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Br:1][C:14]1[C:9]([C:8]2[N:4]([CH3:3])[CH:5]=[N:6][CH:7]=2)=[N:10][C:11]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:20][CH:21]=2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 22273540HCID 22273540, compound

Product 1

HCID 22273571HCID 22273571, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (75.5 mg, 0.47 mmol) was added to a solution of 4-(1-methylimidazol-5-yl)-2-(4-sulphamoylanilino)pyrimidine (Example 15; 0.14 g, 0.42 mmol) and sodium acetate (41.7 mg, 0.51 mmol) in acetic acid (4 ml) and the mixture stirred for 1 hour. The volatiles were evaporated and the residue partitioned between EtOAc and saturated aqueous potassium hydrogen carbonate solution. The organic phase was separated and dried. The residue was pre-absorbed on to silica gel and purified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (9:1) to give the title compound (91 mg, 52%). NMR 10.14 (s, 1H), 8.75 (s, 1H), 7.90-7.69 (m, 4H), 7.17 (s, 2H), 3.84 (s, 3H); m/z 409.

Workup

  1. customThe volatiles were evaporated
  2. customthe residue partitioned between EtOAc and saturated aqueous potassium hydrogen carbonate solution
  3. customThe organic phase was separated
  4. customdried
  5. customThe residue was pre-absorbed on to silica gel
  6. custompurified by column chromatography on silica gel eluting with DCM/2% methanolic ammonia (9:1)

Sources & evidence

ORD record
ord-4c32758a11c04a5487d4f325eeae30d2
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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