Triethylamine → HCID 178496034, compound

HRID 1823796Notes

Reaction equation

HRID 1823796 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([NH:10][C:11]([NH:13][CH2:14][CH2:15][O:16][CH3:17])=[O:12])[NH:7][C:6]=2[CH:18]=1.Cl[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][CH:24]=1)(=[O:22])=[O:21].C(N(CC)CC)C>CC(C)=O>[CH3:17][O:16][CH2:15][CH2:14][NH:13][C:11](=[O:12])[NH:10][C:8]1[NH:9][C:5]2[CH:4]=[CH:3][C:2]([O:1][S:20]([C:23]3[CH:24]=[CH:25][C:26]([O:29][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:27][CH:28]=3)(=[O:22])=[O:21])=[CH:18][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 190100Benzenesulfonyl chloride, 4-(benzoyloxy)-HCID 221469461-(5-hydroxy-1H-benzimidazol-2-yl)-3-(2-methoxyethyl)urea

Product 1

HCID 178496034HCID 178496034, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred solution of 1-(6-hydroxy-1H-benzoimidazol-2-yl)-3-(2-methoxy-ethyl)-urea (31 mg, example 82) and benzoic acid 4-chlorosulfonyl-phenyl ester (37 mg) in acetone (0.6 ml) was treated with triethylamine (33 μl). After stirring at ambient temperature for 4 hours, the reaction mixture was evaporated. The residue was filtered and the filtrate evaporated. The residue was directly purified by LCMS triggered purification to give benzoic acid 4-{2-[3-(2-methoxy-ethyl)-ureido]-1H-benzoimidazol-5-yloxysulfonyl}-phenyl ester (7.2 mg) as a off-white solid Mass spectrum: 511 [M+H]+; retention time=9.90 minutes.

Workup

  1. customthe reaction mixture was evaporated
  2. filtrationThe residue was filtered
  3. customthe filtrate evaporated
  4. customThe residue was directly purified by LCMS
  5. custompurification

Sources & evidence

ORD record
ord-1d2cfb887911478aac47b96b26a5a518
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

Loading…