Methyl N-(triethylammoniosulfonyl)carbamate → HCID 25235813, compound

HRID 1360720Notes

Reaction equation

HRID 1360720 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH:21][C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=O)[CH:15]=[CH:14][C:12]=2[N:13]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]3[O:31][C:22]([C:23]4[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)=[N:21][N:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66966800HCID 66966800, compound

Product 1

HCID 25235813HCID 25235813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 5 mL microwave vial was added 0.2225 g (0.537 mmol) of 4-Methoxy-benzoic acid N′-[2-(2,6-dimethyl-phenyl)-3H-benzoimidazole-5-carbonyl]-hydrazide, 4 mL of THF, and 0.2558 g (1.07 mmol) of burgess reagent. The suspension was placed in the microwave at 150° C. for 15 min. The crude solution was concentrated and the residue was purified by silica gel column chromatography (EtOAc/DCM, 1:9 to 6:4) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.28 (s, 6H) 4.02 (s, 3H) 7.35 (dd, J=15.73, 8.27 Hz, 4H) 7.50 (t, J=7.64 Hz, 1H) 7.87 (d, J=8.34 Hz, 0.5H) 8.04 (d, J=8.46 Hz, 0.5H) 8.15 (dd, J=12.19, 8.65 Hz, 1H) 8.24-8.29 (m, 2H) 8.38 (s, 0.4H) 8.60 (s, 0.5H) 13.15 (d, J=14.27 Hz, 1H). MS (m/z) 397.2 M (+1), tR=1.48, Meth 10

Workup

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

Sources & evidence

ORD record
ord-148e70c354d44ca58b73fab4371d386c
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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