Butyric Acid → HCID 66611299, compound

HRID 76185Notes

Reaction equation

HRID 76185 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.[CH2:38]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]#[C:48][C:49]2[CH:54]=[CH:53][C:52]([CH2:55][CH:56]([NH2:58])[CH3:57])=[CH:51][CH:50]=2)=[CH:43][CH:42]=1)[CH3:39]>CN(C=O)C>[CH2:38]([O:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]#[C:48][C:49]2[CH:50]=[CH:51][C:52]([CH2:55][CH:56]([NH:58][C:1](=[O:6])[CH2:2][CH2:3][CH3:4])[CH3:57])=[CH:53][CH:54]=2)=[CH:43][CH:42]=1)[CH3:39]

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 666104331-(4-((4-Ethoxyphenyl)ethynyl)phenyl)propan-2-amine

Product 1

HCID 66611299HCID 66611299, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.41 mg (0.10 mmol) butanoic acid are dissolved in 300 μL DMF together with 32.1 mg (0.10 mmol) TBTU and 50.0 μL (0.30 mmol) DIPEA and the mixture is stirred at r.t. for 5 min. 27.9 mg (0.10 mmol) 1-(4-((4-ethoxyphenyl)ethynyl)phenyl)propan-2-amine (I64) are added and the reaction mixture is stirred at 40° C. over night. The mixture is filtered through a plug of alox, eluted with DMF/MeOH (9/1) and the solvent is removed in vacuo. The residue is purified by HPLC.

Workup

  1. stirringthe reaction mixture is stirred at 40° C. over night
  2. filtrationThe mixture is filtered through a plug of alox
  3. washeluted with DMF/MeOH (9/1)
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-43976ea5ec50474299f40aefccbbbfe9
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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