HCID 91268953, compound → HCID 2848830, compound

HRID 2389470Notes

Reaction equation

HRID 2389470 reaction equation
C([O:5][C:6](=[O:28])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[S:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][S:17][C:9]2[N:8]([CH2:7][C:6]([OH:28])=[O:5])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 1

HCID 91268953HCID 91268953, compound

Product 1

HCID 2848830HCID 2848830, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution tert-butyl{2-[2-(4-chloro-phenoxy)-ethylsulfanyl]-benzoimidazol-1-yl}-acetate (Precursor D-01b, 33 mg, 0.79 mmol) is stirred in TFA/dichloromethane (1:1, 0.8 ml) at rt for 3 h. The volatiles are removed in vacuo and the residue is purified by flash-chromatography on silica gel (AcOEt/heptane, 1:1; then pure AcOEt), yielding the title compound (27 mg) in 95% as a white solid: tR=5.73 min (LC-1), MS (pos.): m/z 362.8 [M+H]+, MS (neg.): m/z 360.8 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 3.88 (m, 2H, SCH2), 4.22 (t, 2H, OCH2), 4.88 (s, 2H, CH2CO2), 6.54 (d, 2H, Harom), 7.12 (d, 2 Harom), 7.32-7.46 (m, 3Harom), 7.82 (m, 1Harom).

Workup

  1. customThe volatiles are removed in vacuo
  2. customthe residue is purified by flash-chromatography on silica gel (AcOEt/heptane, 1:1

Sources & evidence

ORD record
ord-17273421893b4fb184c6803135d27a0e
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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