Dimethylformamide → HCID 46231335, compound

HRID 1163076Notes

Reaction equation

HRID 1163076 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]3[CH:30]=[CH:29][C:16]([C:17]([N:19]4[CH2:23]C[CH:21](OS(C)(=O)=O)[CH2:20]4)=[O:18])=[CH:15][CH:14]=3)[C:10]3[CH:31]=[CH:32][CH:33]=[CH:34][C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:35]([NH:37][CH3:38])[CH3:36].[CH3:39]N(C=O)C>>[CH2:35]([N:37]([CH3:39])[CH:38]1[CH2:21][CH2:20][N:19]([C:17](=[O:18])[C:16]2[CH:15]=[CH:14][C:13]([CH2:12][N:11]3[C:10]4[CH:31]=[CH:32][CH:33]=[CH:34][C:9]=4[N:8]=[C:7]3[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:30][CH:29]=2)[CH2:23]1)[CH3:36]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 12219N-MethylethylamineHCID 58970771HCID 58970771, compound

Product 1

HCID 46231335HCID 46231335, compound

Procedure

A solution of methanesulfonic acid 1-[4-(2-phenyl-benzoimidazol-1-ylmethyl)-benzoyl]-pyrrolidin-3-yl ester (71 mg, 0.15 mmol) in DMF is treated with N-ethylmethylamine (0.038 mL, 0.45 mmol), stirred at room temperature overnight and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL) and purified by reverse-phase semi-preparative HPLC1 to give the title product as a white powder (6.4 mg), identified by HPLC2 and MS [439.6 m/e (M+H)], retention time 1.48 min.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of DMSO, MeOH and water (1.5 mL)
  3. custompurified by reverse-phase semi-preparative HPLC1

Sources & evidence

ORD record
ord-b8ce269dcec84780819704421656ec39
Source dataset
uspto-grants-2010_10
Patent number
US07820825B2

Reaction notes

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