1,2,3,4-Tetrahydroisoquinoline → HCID 59170171, compound

HRID 1446313Notes

Reaction equation

HRID 1446313 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:23][C:24]1[C:28]([C:29]([OH:31])=O)=[C:27]([CH2:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:26][N:25]=1.C(N(C(C)C)C(C)C)C.[CH2:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:53][CH2:52][NH:51]1>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:50]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[CH2:53][CH2:52][N:51]1[C:29]([C:28]1[C:24]([CH3:23])=[N:25][O:26][C:27]=1[CH2:32][C:33]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:40])=[O:31]

Participants

7

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 45123112HCID 45123112, compound

Product 1

HCID 59170171HCID 59170171, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of TBTU (0.48 g, 1.5 mmol, 1.5 eq.) in DMF (2 mL) was added to a mixture of 3-methyl-5-(2-oxo-2-phenylethyl)isoxazole-4-carboxylic acid (0.24 g, 1 mmol, 1 eq), N-ethyl-N-isopropylpropan-2-amine (0.18 mL, 1 eq) and 1,2,3,4-tetrahydroisoquinoline (0.12 mL, 1 eq) in DMF (1 mL). The resulting solution was stirred at room temperature. Chloroform (25 mL) was added and the solution was washed with water and 1 M HCl, dried (Na2SO4) and evaporated. The residue was purified by flash chromatography (SiO2 1:2 heptane/EtOAc) to afford the title compound. MS (ESI, POS. ION) M/Z Calcd for C22H20N2O3: 360.1474, found 360.1472.

Workup

  1. washthe solution was washed with water and 1 M HCl
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by flash chromatography (SiO2 1:2 heptane/EtOAc)

Sources & evidence

ORD record
ord-86f63014529e49aa99139695720402a7
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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