Triethylamine → HCID 15104691, compound

HRID 2115093Notes

Reaction equation

HRID 2115093 reaction equation
Cl.[CH2:2]([CH:9]1[CH2:14][CH2:13][N:12]([CH:15]([CH3:19])[C:16]([OH:18])=[O:17])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:20](N(CC)CC)[CH3:21].NC1C=CC2NC(=O)OC=2C=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O>[CH2:20]([O:17][C:16](=[O:18])[CH:15]([N:12]1[CH2:11][CH2:10][CH:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:14][CH2:13]1)[CH3:19])[CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8269896-amino-1,3-benzoxazol-2(3H)-oneHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 52983846HCID 52983846, compound

Product 1

HCID 15104691HCID 15104691, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.5 g (2.0 mmol) of 2-(4-benzyl-piperidin-1-yl)-propionic acid hydrochloride, 0.3 ml (2.1 mmol) of triethylamine, 0.36 g (2.0 mmol) of 6-amino-3H-benzoxazol-2-one, 0.8 g (2.1 mmol) of HBTU and 10 ml of dimethylformamide is stirred at room temperature for 24 hours. The reaction mixture is concentrated and the residue is purified by column chromatography using Kieselgel 60 (Merck) as adsorbent and toluene:methanol=4:1 as eluent. The product is crystallized with diethylether to yield 0.095 g (11.6%) of the title compound. Melting Point: 116-118° C. (diethylether).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography
  3. customThe product is crystallized with diethylether

Sources & evidence

ORD record
ord-34f5226cc2114027898966ede040070f
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

Loading…