Chlorosulfonyl isocyanate → HCID 178435872, compound

HRID 2174019Notes

Reaction equation

HRID 2174019 reaction equation
[CH2:1]([C:3]1[C:4]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=3[N:15]=2)=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[CH:6]2)[CH3:2].ClS([N:29]=[C:30]=O)(=O)=O>CN(C=O)C>[C:30]([C:6]1[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=[C:3]([CH2:1][CH3:2])[C:4]=2[CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=3[N:15]=2)[NH:8][CH:7]=1)#[N:29]

Participants

4

Reactant 2

HCID 70918Chlorosulfonyl isocyanateHCID 178435865HCID 178435865, compound

Product 1

HCID 178435872HCID 178435872, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-((5-ethyl-7-methyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (15 mg, 0.048 mmol) in DMF (1 mL) was added chlorosulfonyl isocyanate (17 μL, 0.191 mmol) at 0° C., and then the mixture was stirred at 0° C. for 1.5 h. The mixture was allowed to warm up to room temperature with stirring. After 13.5 h, the reaction was quenched by 28% aq. NH4OH. The mixture was stirred for 0.25 h and then extracted with EtOAc/2,2,2-trifluoroethanol (c.a. 9/1). The organic layer was washed with H2O and brine, dried over Na2SO4, and filtered. After concentration, the resulting residue was purified by silica gel flash column chromatography [CH2Cl2/(2M NH3 in MeOH)=98/2, isocratic] to give the title compound. 1H NMR (400 MHz, ACETONITRILE-d3 with about 5 μL TFA) δ ppm 10.22 (br. s., 1H), 8.07 (dd, J=1.00, 1.10 Hz, 1H), 7.91 (d, J=3.16 Hz, 1H), 7.71-7.85 (m, 2H), 7.15 (s, 1H), 5.02 (s, 2H), 2.71 (q, J=7.60 Hz, 2H), 2.54 (d, J=0.63 Hz, 3H), 1.14 (t, J=7.58 Hz, 3H). HRMS calcd. for C21H17N5 (M+H)+ 340.1557. found 340.1556.

Workup

  1. temperatureto warm up to room temperature
  2. stirringwith stirring
  3. waitAfter 13.5 h
  4. customthe reaction was quenched by 28% aq. NH4OH
  5. stirringThe mixture was stirred for 0.25 h
  6. extractionextracted with EtOAc/2,2,2-trifluoroethanol (c.a. 9/1)
  7. washThe organic layer was washed with H2O and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationAfter concentration
  11. customthe resulting residue was purified by silica gel flash column chromatography [CH2Cl2/(2M NH3 in MeOH)=98/2, isocratic]

Sources & evidence

ORD record
ord-0428149935274e0a809052df4304bf39
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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