Pyrrolidine → HCID 178502037, compound

HRID 1823779Notes

Reaction equation

HRID 1823779 reaction equation
[CH3:1][O:2][C:3]([NH:5][C:6]1[NH:7][C:8]2[CH:14]=[C:13]([O:15][S:16]([C:19]3[CH:29]=[CH:28][C:22]([O:23][CH2:24][C:25](O)=[O:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:12]=[CH:11][C:9]=2[N:10]=1)=[O:4].[CH:30]([N:33]([CH:36]([CH3:38])C)CC)([CH3:32])C.N1CCCC1>CN(C)C=O>[CH3:1][O:2][C:3]([NH:5][C:6]1[NH:10][C:9]2[CH:11]=[CH:12][C:13]([O:15][S:16]([C:19]3[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25](=[O:26])[N:33]4[CH2:30][CH2:32][CH2:38][CH2:36]4)=[CH:28][CH:29]=3)(=[O:18])=[O:17])=[CH:14][C:8]=2[N:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 22146800HCID 22146800, compound

Product 1

HCID 178502037HCID 178502037, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of [4-(2-methoxycarbonylamino-3H-benzoimidazol-5-yloxysulfonyl)-phenoxy]-acetic acid (40 mg, example 64-e) in dry dimethylformamide (3 ml) was treated with N-{(dimethylamino)(1H-1,2,3-triazolo[4,5-b]pyridin-1-yl)methylene}-N-methylmethanaminium hexafluorophosphate N-oxide (39 mg) and diisopropylethylamine (50 μl). After stirring at ambient temperature for 30 minutes, pyrrolidine (21 μl) was added and the mixture stirred at room temperature for a further 3 hours. The solvent was removed in vacuo and the residue was purified by triggered LC/MS to give 4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)-benzenesulfonic acid 2-methoxycarbonylamino-1H-benzoimidazol-5-yl-ester as an off-white solid. Mass spectrum: 475[M+H]+; retention time=8.39 minutes.

Workup

  1. stirringthe mixture stirred at room temperature for a further 3 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by triggered LC/MS

Sources & evidence

ORD record
ord-32af694fca204e44b1195b5d582d892c
Source dataset
uspto-grants-2006_05
Patent number
US07041668B2

Reaction notes

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