Bromine → HCID 17933126, compound

HRID 2375293Notes

Reaction equation

[Br:1]Br.[CH2:3]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([S:23](=[O:30])(=[O:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=3)[N:11]=2)=[CH:8][N:7]=[C:6]1[CH3:31])[CH3:4]>C(O)(=O)C>[Br:1][C:15]1[C:10]([C:9]2[N:5]([CH2:3][CH3:4])[C:6]([CH3:31])=[N:7][CH:8]=2)=[N:11][C:12]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([S:23](=[O:30])(=[O:29])[NH:24][CH2:25][CH2:26][O:27][CH3:28])=[CH:21][CH:22]=2)=[N:13][CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Bromine (8 μl, 0.14 mmol) was added to a solution of 4-(1-ethyl-2-methylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine (Method 71; 52 mg, 0.13 mmol) in glacial acetic acid (2 ml) heated at 60° C. The mixture was heated at 60° C. for 4 hours, then the solvent was removed by evaporated. The residue was dissolved in DCM (20 ml), washed with saturated aqueous sodium hydrogen carbonate solution (20 ml), dried (Chemelut column 1005) and purified by flash chromatography eluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 97:3) to yield the title compound (37 mg, 60%) as a white foam NMR 1.25 (t, 3H), 2.50 (s, 3H), 3.15 (q, 2H), 3.26 (s, 3H), 3.42 (t, 2H), 4.33 (q, 2H), 4.92 (t, 1H), 7.40 (s, 1H), 7.71 (d, 2H), 7.82 (m, 3H), 8.61 (s, 1H); m/z 497.

Workup

temperatureThe mixture was heated at 60° C. for 4 hours
customthe solvent was removed
customby evaporated
dissolutionThe residue was dissolved in DCM (20 ml)
washwashed with saturated aqueous sodium hydrogen carbonate solution (20 ml)
customdried (Chemelut column 1005)
custompurified by flash chromatography
washeluting with DCM/2% methanolic ammonia (100:0 increasing in polarity to 97:3)

Sources & evidence

ORD record: ord-c7144c93b7d044d399b2b75a66098623
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465728B2

Reaction notes

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