Triethylamine → HCID 53308074, compound

HRID 1846660Notes

Reaction equation

HRID 1846660 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([NH:7][C:8]1[C:9]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23](O)=[O:24])[CH2:18][CH2:17]2)=[N:10][CH:11]=[C:12]([C:14]#[N:15])[CH:13]=1)=[O:6].[OH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.[B-](F)(F)(F)F.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.C(N(CC)CC)C>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:26]=[CH:27][CH:28]=1)[C:5]([NH:7][C:8]1[C:9]([N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]([N:33]3[CH2:34][CH2:35][CH:30]([OH:29])[CH2:31][CH2:32]3)=[O:24])[CH2:18][CH2:17]2)=[N:10][CH:11]=[C:12]([C:14]#[N:15])[CH:13]=1)=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 71238166HCID 71238166, compound

Product 1

HCID 53308074HCID 53308074, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.015 g (0.038 mmol) of [3′-(3-chloro-benzoylamino)-5′-cyano-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid, 0.019 g (0.19 mmol) of 4-hydroxypiperdine, 0.016 g (0.049 mmol) of 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, and 0.016 mL (0.11 mmol) of triethylamine in N,N-dimethylformamide (2 mL) is allowed to stir at room temperature overnight. The mixture is concentrated under reduced pressure and the residue is diluted with water which results in a solid precipitating. The light red solid is collected by filtration and washed with water. The collected material is purified using preparative reverse phase HPLC to give 0.011 g (61%) of the title compound (145) as a colorless solid. [M+H]+=482.2

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. additionthe residue is diluted with water which
  3. customresults in a solid
  4. customprecipitating
  5. filtrationThe light red solid is collected by filtration
  6. washwashed with water
  7. customThe collected material is purified

Sources & evidence

ORD record
ord-add61ec43bb14f49b76e7123aa75d33f
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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