2-(5-Chlorothiophen-2-yl)ethenesulfonyl chloride → HCID 69205959, compound

HRID 970642Notes

Reaction equation

HRID 970642 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[CH:17][N:16]=[C:15]3[CH2:19][N:20]([CH3:22])[CH3:21])=[CH:10][C:9]=2[F:23])[C:3]1=[O:24].[Cl:25][C:26]1[S:30][C:29]([CH:31]=[CH:32][S:33](Cl)(=[O:35])=[O:34])=[CH:28][CH:27]=1>C(Cl)Cl>[Cl:25][C:26]1[S:30][C:29]([CH:31]=[CH:32][S:33]([NH:1][N:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]3[CH:13]=[CH:12][C:11]([N:14]4[CH:18]=[CH:17][N:16]=[C:15]4[CH2:19][N:20]([CH3:21])[CH3:22])=[CH:10][C:9]=3[F:23])[C:3]2=[O:24])(=[O:35])=[O:34])=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chlorideHCID 58787213HCID 58787213, compound

Product 1

HCID 69205959HCID 69205959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

18.6 mg (0.046 mmol) of the diHCl salt of 1-amino-3-(4-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-2-fluorophenyl)-tetrahydropyrimidin-2(1H)-one prepared as above, were dissolved in 3 mL of anhydrous CH2Cl2. To this solution placed under N2 atmosphere were added 50 μL of TEA followed by 11.2 mg (0.046 mmol) of 2-(5-chlorothiophen-2-yl)ethenesulfonyl chloride. The mixture was stirred at room temperature overnight. An additional 3 mL of CH2Cl2 were added, and the mixture was washed twice with 2 mL of saturated NaHCO3 solution. The organic phase was dried and concentrated to yield 17.2 mg of a brown oil. A pure compound was obtained after purification by preparative HPLC. 1H NMR (500 MHz, MeOD) δ 7.53 (t, 1H), 7.49 (s, 1H) 7.41 (d, J=10.4 Hz, 1H), 7.29 (s, 1H), 7.27 (d, J=8.2 Hz, 1H), 6.93(d, J=3.8 Hz, 1H), 6.86 (d, J=3.8 Hz, 1H), 5.1 (m, 1H), 4.45 (q, 2H), 3.5 (m, 2H), 3.14 (m, 1H), 2.86 (s, 6H), 2.0 (m, 2H), ppm. LC-MS (ESI) 556.8 [M+NH4+, tR=4.645 min (Shimadzu Phenomenex S5 ODS 4.6×50 mm Luna flow rate 2.5 ml/mn; detection at 220 nM; Gradient elution 0% to 100% B over 8 min; (A=10% MeOH, 90% H2O, 0.2% H3PO4& B=90% MeOH, 10% H2O, 0.2% H3PO4). HRMS (ESI) m/z calcd for C22H25ClFN6O3S2 [M+H]+ 539.1102. found 539.1105

Workup

  1. washthe mixture was washed twice with 2 mL of saturated NaHCO3 solution
  2. customThe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-30e27654b2d449fb912e664d656f25a9
Source dataset
uspto-grants-2007_12
Patent number
US07312218B2

Reaction notes

Loading…