Diisopropylethylamine → HCID 59170141, compound

HRID 1446274Notes

Reaction equation

HRID 1446274 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=N[C:26]2C=CC=C[C:25]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.[NH:47]1[CH2:52][CH2:51][CH2:50][CH:49]([C:53]([O-:55])=[O:54])[CH2:48]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:47]2[CH2:52][CH2:51][CH2:50][CH:49]([C:53]([O:55][CH2:25][CH3:26])=[O:54])[CH2:48]2)=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22647218HCID 22647218, compoundHCID 228317065-(p-Tolyl)isoxazole-4-carboxylic acid

Product 1

HCID 59170141HCID 59170141, compoundYield 58.4%

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, 0.10 mmol, 2 equ) in DMF (0.3 mL) was added to piperidine-3-carboxylate (8 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 (10 mg). MS (ESI, pos. ion) m/z calcd for C19H22N2O4: 342.1580, found 342.1585

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-17ee0a235af64f4aaac559c68cf5bfa6
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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