Methanol → HCID 18626916, compound

HRID 1860242Notes

Reaction equation

CO.[Br:3][C:4]1[CH:5]=[C:6]([C:10]([NH:12][CH2:13][CH2:14]CO)=[O:11])[NH:7][C:8]=1[Br:9].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C>C1COCC1>[Br:9][C:8]1[NH:7][C:6]([C:10]2[O:11][CH2:14][CH2:13][N:12]=2)=[CH:5][C:4]=1[Br:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Method A. A solution of 10 (0.25 g, 0.77 mmol) in 2 mL of methanesulfonic acid was heated at 60° C. for 3 d. The reaction mixture was diluted with ether (100 mL) and washed with sat. NaHCO3 (20 mL×3) and sat. NaCl (20 mL). The organic layer was dried (MgSO4) and evaporated under reduced pressure. The resulting residue was purified by flash chromatography (EtOAc/hexanes 1:1) to give 14 (0.14 g, 59%) as a colorless solid: 1H NMR (CDCl3) d 2.00 (p, 2H, J=5.7), 3.52 (t, 2H, J=5.7), 4.32 (t, 2H, J=5.7), 6.58 (s, 1H), 10.10 (br, 1H); 13C NMR (CD3COCD3) d 22.2 (e), 41.3 (e), 66.6 (e), 99.1 (e), 109.4 (e), 115.0 (o), 127.7 (e), 153.8 (e); UV (CH3OH) lmax 329, 275 nm; MS m/z (relative intensity) 311 (M++5, 50), 309 (M++3, 100), 307 (M++1, 50); Anal. Calcd for C8H8N2OBr2: C, 31.20; H, 2.62; N, 9.10; Found: C, 31.17; H, 2.51; N, 9.29. Method B. To a stirred mixture of 10 (0.25 g, 0.77 mmol) and p-toluenesulfonyl chloride (0.16 g, 0.77 mmol) in 10 mL of THF was added triethylamine (0.6 mL, 4.27 mmol) at room temperature. The mixture was heated at 80° C. overnight. The solvent was evaporated under reduced pressure and the resulting residue was purified by flash chromatography (CH2Cl2/MeOH 19:1) to give 14 (0.15 g, 63%) as a colorless solid.

Workup

customThe solvent was evaporated under reduced pressure
customthe resulting residue was purified by flash chromatography (CH2Cl2/MeOH 19:1)

Sources & evidence

ORD record: ord-877844fc76b741a996da673ac55a30c0
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06528646B2

Reaction notes

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