Methyl N-(triethylammoniosulfonyl)carbamate → HCID 66966785, compound

HRID 1360763Notes

Reaction equation

HRID 1360763 reaction equation
[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]([NH:24][NH:25][C:26](=O)[C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)=[O:23])[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[CH3:1][O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]4[O:23][C:26]([C:27]5[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=5)=[N:25][N:24]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 66966773HCID 66966773, compound

Product 1

HCID 66966785HCID 66966785, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 5 mL microwave vial was added 0.2010 g (0.369 mmol) of (4-{6-[N′-(4-Chloro-benzoyl)-hydrazinocarbonyl]-1H-benzoimidazol-2-yl}-3,5-dimethyl-phenoxy)-acetic acid methyl ester, 5 mL of THF, and 0.1890 g (0.793 mmol) of burgess reagent. The suspension was placed in the microwave at 150° C. for 20 min. The brownish solution was concentrated and the residue was purified by silica gel (ACN/DCM, 1:9 to 5:5) to give the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.10 (s, 6H) 3.72 (s, 4H) 4.86 (s, 2H) 6.81 (s, 2H) 7.68-7.74 (m, 2.5H) 7.87 (d, J=8.46 Hz, 0.5H) 7.97-8.04 (m, 1H) 8.15-8.24 (m, 2.5H) 8.45 (s, 0.5H) 12.93 (d, J=15.66 Hz, 1H). MS (m/z) 489.1 M (+1), tR=1.40, Meth 10

Workup

  1. concentrationThe brownish solution was concentrated
  2. customthe residue was purified by silica gel (ACN/DCM, 1:9 to 5:5)

Sources & evidence

ORD record
ord-3f1aa1c803ff4aa8ad1577fc087e351b
Source dataset
uspto-grants-2011_02
Patent number
US07879850B2

Reaction notes

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