Diisopropylethylamine → HCID 59170043, compound

HRID 1446270Notes

Reaction equation

HRID 1446270 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([O:23]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(C(C)C)C(C)C)C.Cl.[C:48]1([CH:54]2[CH2:58][CH2:57][NH:56][CH2:55]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH: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:56]2[CH2:57][CH2:58][C:54]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)([OH:23])[CH2:55]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 441188043-Phenylpyrrolidine--hydrogen chloride (1/1)

Product 1

HCID 59170043HCID 59170043, compoundYield 40.2%

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 (26 μL, 0.15 mmol, 3 equ) in DMF (0.3 mL) was added to 3-phenylpyrrolidine 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 (7 mg). MS (ESI, pos. ion) m/z calcd for C21H20N2O3: 348.1474, found 348.1470.

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-4f3a6144582d4a7e87cbdc19aa4cf675
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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