Diisopropylethylamine → 3-(1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)pentan-3-ol

HRID 1446273Notes

Reaction equation

HRID 1446273 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([OH:15])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.Cl.[NH:48]1[CH2:53][CH2:52][CH2:51][CH:50]([C:54]([OH:59])([CH2:57][CH3:58])[CH2:55][CH3:56])[CH2:49]1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[C:13]([N:48]2[CH2:53][CH2:52][CH2:51][CH:50]([C:54]([OH:59])([CH2:57][CH3:58])[CH2:55][CH3:56])[CH2:49]2)=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acidHCID 686828543-Piperidin-3-ylpentan-3-ol hydrochloride

Product 1

HCID 591701223-(1-{[5-(4-Methylphenyl)isoxazol-4-yl]carbonyl}piperidin-3-yl)pentan-3-olYield 44.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(4-methylphenyl)isoxazole-4-carboxylic acid (10 mg, 0.05 mmol), TBTU (19 mg, 0.06 mmol, 1,2 equ.) and N-ethyl-N-isopropylpropan-2-amine (17 μL, 0.010 mmol, 2 equ) in DMF (0.3 mL) was added to 3-piperidin-3-ylpentan-3-ol hydrochloride (10 mg, 0.05 mmol) and the reaction mixture was left at rt for 2 h. The solvent was evaporated and the crude product was purified by RP-HPLC. After evaporation of the solvents the product was dried in vacuum to yield the title compound (8 mg). MS (ESI, pos. ion) m/z calcd for C21H28N2O3: 356.2100, found 356.2099.

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was purified by RP-HPLC
  3. customAfter evaporation of the solvents the product
  4. customwas dried in vacuum

Sources & evidence

ORD record
ord-4b5f4b2e832f4905a8ca021ae7c2433a
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

Loading…