Methyl N-(triethylammoniosulfonyl)carbamate → HCID 25235717, compound

HRID 1360716Notes

Reaction equation

HRID 1360716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH:21][C:22](=O)[C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]2[O:19][C:18]([C:16]3[CH:15]=[CH:14][C:12]4[N:13]=[C:9]([C:3]5[C:4]([Cl:8])=[CH:5][CH:6]=[CH:7][C:2]=5[Cl:1])[NH:10][C:11]=4[CH:17]=3)=[N:20][N:21]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66966781HCID 66966781, compound

Product 1

HCID 25235717HCID 25235717, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 20 mL microwave vial was added 0.500 g (1.09 mmol) of 4-Chloro-benzoic acid N′-[2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazide, 13 mL of THF, and 0.5187 g (2.18 mmol) of Burgess Reagent. The suspension was placed in the microwave at 150° C. for 20 min. The crude solution was concentrated and the residue was purified by silica gel column chromatography (ACN/DCM, 1:9 to 6:4) to give of the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.62-7.67 (m, 1H) 7.68-7.74 (m, 4.5H) 7.78-7.81 (m, 0.6H) 7.94 (d, J=8.46 Hz, 0.5H) 8.02-8.10 (m, 1H) 8.17-8.22 (m, 2H) 8.33 (d, J=1.01 Hz, 0.4H) 8.49-8.52 (m, 0.6H) 13.36 (d, J=10.36 Hz, 1H). MS (m/z) 442.9 M (+1), tR=1.49, Meth 10

Workup

  1. concentrationThe crude solution was concentrated
  2. customthe residue was purified by silica gel column chromatography (ACN/DCM, 1:9 to 6:4)

Sources & evidence

ORD record
ord-b73489da09de4d3a9fa7e5df4b60a882
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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