HCID 86620034, compound → HCID 11653075, compound

HRID 2389505Notes

Reaction equation

HRID 2389505 reaction equation
[CH2:1]([S:8][C:9]1[N:13]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[C:12]2[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.ClCCl>[CH2:1]([S:8][C:9]1[N:13]([CH2:14][C:15]([OH:17])=[O:16])[C:12]2[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:11]=2[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86620034HCID 86620034, compound

Product 1

HCID 11653075HCID 11653075, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl (2-benzylsulfanyl-5-nitro-benzoimidazol-1-yl)-acetate (Precursor 5-NO2-C-02b, 20 mg, 0.05 mmol) is dissolved in TFA/dichloromethane (1:1, 0.5 ml) and stirred for 2 h at rt. The solvents are evaporated under a stream of air and Et2O (1 ml) is added to the crude mixture. The solid obtained is filtered, rinsed twice with Et2O and dried under high vacuum yielding the title compound (10.4 mg) in 60% as a slightly yellow solid: tR=6.30 min (LC-1), ESI-MS (pos.): m/z 344.23 [M+H]+, ESI-MS (neg.): m/z 342.34 [M−H]+; 1H-NMR (DMSO-d6): δ (ppm) 4.66 (s, 2H, SCH2), 5.07 (s, 2H, CH2CO2), 7.23-7.33 (m, 3Harom), 7.46 (dd, 2Harom), 7.74 (d, 1Harom), 8.13 (dd, 1 Harom), 8.44 (d, 1Harom).

Workup

  1. customThe solvents are evaporated under a stream of air and Et2O (1 ml)
  2. additionis added to the crude mixture
  3. customThe solid obtained
  4. filtrationis filtered
  5. washrinsed twice with Et2O
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-7339ece8ad4b4d4ba60144b848f9feb7
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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