Trifluoroacetic acid → HCID 22273484, compound

HRID 1064317Notes

Reaction equation

HRID 1064317 reaction equation
[Cl:1][C:2]1[C:3]([C:23]2[N:27]([CH3:28])[C:26]([CH3:29])=[N:25][CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:22])(=[O:21])[NH:16]C(C)(C)C)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>O>[Cl:1][C:2]1[C:3]([C:23]2[N:27]([CH3:28])[C:26]([CH3:29])=[N:25][CH:24]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](=[O:21])(=[O:22])[NH2:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 22273579HCID 22273579, compound

Product 1

HCID 22273484HCID 22273484, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-chloro-4-(1,2-dimethylimidazol-5-yl)-2-{4-[N-(t-butyl)sulphamoyl]anilino}pyrimidine (Example 60; 116 mg, 0.267 mmol), trifluoroacetic acid (2.7 ml), water (0.3 ml) and anisole (145 μl, 1.34 mmol) was stirred at ambient temperature for 72 hours. The mixture was then concentrated by evaporation and the residue treated with water and ether. The precipitated solid was collected by filtration, washed with water and ether, and dried to give the title compound (87 mg, 86%) as a white solid. NMR: 2.4 (s, 3H), 3.78 (s, 3H), 7.15 (s, 2H), 7.65 (s, 1H), 7.73 (d, 2H), 7.83 (d, 2H), 8.6 (s, 1H), 10.11 (s, 1H); m/z 3.78 (M−H)−.

Workup

  1. concentrationThe mixture was then concentrated by evaporation
  2. additionthe residue treated with water and ether
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water and ether
  5. customdried

Sources & evidence

ORD record
ord-fcaf49210add4c02a088ad8184a7a193
Source dataset
uspto-grants-2005_11
Patent number
US06969714B2

Reaction notes

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