Dimethylamine → HCID 12988790, compound

HRID 392614Notes

Reaction equation

HRID 392614 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[NH:8][C:9]2[CH:15]=[C:14]([C:16]([OH:18])=O)[CH:13]=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].[CH3:19][N:20](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:21].F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.CNC>C1COCC1>[CH3:19][N:20]([CH3:21])[C:16]([C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[C:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[NH:8][C:9]=2[CH:15]=1)=[O:18]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12988789HCID 12988789, compound

Product 1

HCID 12988790HCID 12988790, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-[(Ethoxycarbonyl)methyl]benzimidazole-5-carboxylic acid (1.0 eq) was dissolved in THF. HBTU (1.1 eq) and diisopropylethylamine (2.0 eq) were added, followed by dimethylamine (2.0 M in THF, 1.1 eq). The reaction was stirred at room temperature overnight then concentrated and the resulting residue was purified by silica gel chromatography (5:95 MeOH:CH2Cl2) to afford the desired compound. LC/MS m/z 276.2 (MH+), Rf 1.18 minutes.

Workup

  1. concentrationthen concentrated
  2. customthe resulting residue was purified by silica gel chromatography (5:95 MeOH:CH2Cl2)

Sources & evidence

ORD record
ord-ca71003b9ac14c9bad6e37d439dcf8c1
Source dataset
uspto-grants-2004_10
Patent number
US06800760B2

Reaction notes

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