Chlorosuccinimide → HCID 57722906, compound

HRID 1987135Notes

Reaction equation

HRID 1987135 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][N:10]([CH3:37])[S:11]([NH:14][C:15]1[CH:16]=[CH:17][C:18]2[CH:34]=[CH:33][C:22]3=[N:23][CH:24]=[C:25]([C:27]4[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=4)[CH:26]=[C:21]3[C:20](=[O:35])[C:19]=2[CH:36]=1)(=[O:13])=[O:12].C(=O)([O-])O.[Na+]>C(#N)C>[Cl:1][C:33]1[C:22]2=[N:23][CH:24]=[C:25]([C:27]3[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=3)[CH:26]=[C:21]2[C:20](=[O:35])[C:19]2[CH:36]=[C:15]([NH:14][S:11]([N:10]([CH3:37])[CH3:9])(=[O:13])=[O:12])[CH:16]=[CH:17][C:18]=2[CH:34]=1

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 516892Sodium BicarbonateHCID 16222392HCID 16222392, compound2×

Product 1

HCID 57722906HCID 57722906, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

N-Chlorosuccinimide (30.6 mg, 0.229 mmol) was added to N,N-dimethyl-N′-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]sulfamide (Compound 118) (75 mg, 0.183 mmol) suspended in acetonitrile (18.3 ml) at room temperature. The resulting suspension was heated to 100° C. in a sealed vial for 24 h. After standing at room temperature for an additional 2 days, the reaction was basified with aqueous sodium hydrogen carbonate (saturated, 75 mL) and extracted with dichloromethane (2×50 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC reverse phase (C-18), eluting with acetonitrile/water+0.1% TFA, to afford the title compound as a yellow/orange solid. 1H NMR (600 MHz, CDCl3) δ 9.10 (d, 1H, J=1.8 Hz); 8.45 (d, 1H, J=2.4 Hz); 7.94 (d, 1H, J=0.6 Hz); 7.83 (s, 1H); 7.79 (d, 1H, J=2.4 Hz); 7.68 (s, 1H); 7.55 (dd, 1H, J=8.4, 2.4 Hz); 7.50 (d, 1H, J=9.0 Hz); 7.03 (s, 1H); 4.00 (s, 3H); 2.91 (s, 6H). LCMS (APCI) exact mass calc'd for [M+H]+ (C20H18ClN5O3S) requires m/z 444.1 found 444.1.

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe combined organics were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC reverse phase (C-18)
  6. washeluting with acetonitrile/water+0.1% TFA

Sources & evidence

ORD record
ord-e38fa7a09a944912bac7734d76f90554
Source dataset
uspto-grants-2009_06
Patent number
US07550478B2

Reaction notes

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