Triethylamine → HCID 68511079, compound

HRID 2094830Notes

Reaction equation

HRID 2094830 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 over-night. 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. waitto shake at room temperature over-night
  3. concentrationThe mixture was then concentrated in vacuo
  4. dissolutiondissolved in 1.4 ml of DMSO/methanol (1:1 v/v)
  5. customsubmitted for reverse phase purification

Sources & evidence

ORD record
ord-67682b0f4c194c3db2f4a67ce0e520be
Source dataset
uspto-grants-2013_05
Patent number
US08445686B2

Reaction notes

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