Triethylamine → HCID 68511079, compound

HRID 341256Notes

Reaction equation

HRID 341256 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:48]1([C@H:54]([NH2:56])[CH3:55])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CC(N(C)C)=O>[Cl:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:56][C@@H:54]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[CH3:55])=[O:6]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 6431891-Phenethylamine, (+)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10353958HCID 10353958, compound

Product 1

HCID 68511079HCID 68511079, compoundYield 70.74%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Procedure

A 20-ml scintillation vial was charged with a solution of 2-chloro-4-(pyridin-4-yl)benzoic acid in DMA (20.0 mg, 0.085 mmol, 1.0 eq), a solution of HATU in DMA (39.06 mg, 0.103 mmol, 1.20 eq), and triethylamine (28.83 μL, 0.205 mmol, 2.40 eq). The mixture was briefly shaken and a solution of (R)-1-phenylethanamine (14.52 mg, 0.1198 mmol, 1.40 eq) in DMA was added. The mixture was left to shake at room temperature overnight. The mixture was then concentrated in vacuo and dissolved in 1.4 ml of DMSO/methanol (1:1 v/v) and submitted for reverse phase purification to afford (R)-2-chloro-N-(1-phenylethyl)-4-(pyridin-4-yl)benzamide (27.30 mg, 70.74% yield).

Workup

  1. waitThe mixture was left
  2. concentrationThe mixture was then concentrated in vacuo
  3. dissolutiondissolved in 1.4 ml of DMSO/methanol (1:1 v/v)
  4. customsubmitted for reverse phase purification

Sources & evidence

ORD record
ord-9550707b79024fc7a20b80e6c2292058
Source dataset
uspto-grants-2014_11
Patent number
US08895749B2

Reaction notes

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