Triethylamine → HCID 9862547, compound

HRID 900818Notes

Reaction equation

HRID 900818 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C:10]([OH:12])=O)[NH:7][C:6]=2[CH:13]=1.C(N(CC)CC)C.[CH2:21]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH2:21]([CH:28]1[CH2:33][CH2:32][N:31]([C:10]([C:8]2[NH:7][C:6]3[CH:13]=[C:2]([OH:1])[CH:3]=[CH:4][C:5]=3[N:9]=2)=[O:12])[CH2:30][CH2:29]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 317384-BenzylpiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223501686-Hydroxy-1H-benzimidazole-2-carboxylic acid

Product 1

HCID 9862547HCID 9862547, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3.0 g (16.75 mmol) of 6-hydroxy-1H-benzoimidazol-2-carboxilic acid, 2.4 ml (17.2 mmol) of triethylamin, 3.0 g (17.1 mmol) of 4-benzyl-piperidine, 7.0 g (18.5 mmol) of HBTU and 100 ml of dimethylformamide is stirred at room temperature for 16 h. The reaction mixture is concentrated and the residue is purified by column chromatography using Kieselgel 60 as adsorbent (Merck) and toluene:methanol=4:1 as eluent, then the product is recrystallized from toluene to yield 3.58 g (63.5%) of the title compound. Mp.: 186° C. (toluene).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography
  3. custommethanol=4:1 as eluent, then the product is recrystallized from toluene

Sources & evidence

ORD record
ord-70d7c3f4f2aa425782051e483dfd8186
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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