Ethyl Acetate → HCID 59511138, compound

HRID 1157141Notes

Reaction equation

HRID 1157141 reaction equation
CCN(C(C)C)C(C)C.[C:10]1([C:20]([OH:22])=O)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1.CN(C(O[N:31]1N=N[C:33]2[CH:34]=[CH:35]C=C[C:32]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[C:45]([O:48][CH2:49]C)(=[O:47])[CH3:46]>CN(C=O)C>[CH3:49][O:48][C:45]([C@@H:46]1[CH2:35][CH2:34][CH2:33][CH2:32][N:31]1[C:20]([C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][N:11]=1)=[O:22])=[O:47]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 68092Isoquinoline-1-carboxylic acidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 59511138HCID 59511138, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of (S)-1-Piperidine-carboxylic acid methyl ester hydrochloride (1.00 g, 5.57 mmol), in DMF (20 ml) at room temperature was treated with DIPEA (2.12 ml, 12.25 mmol). The resulting mixture was allowed to stir for 30 min before being treated with 1-isoquinolinecarboxylic acid (964 mg, 5.57 mmol) and TBTU (1.79 g, 5.57 mmol). The mixture stirred at room temperature for 4 hr, diluted with ethyl acetate, washed with saturated aq. NaHCO3, saturated aq. NaCl, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (67% ethyl acetate in hexane) to afford the sub-title compound as a colourless gum (1.05 g, 63%): 1H NMR (400 MHz, CDCl3) δ 1.00-2.51 (6H, m), 3.05-3.38 (2H, m), 3.60-3.95 (3H, m), 4.35-4.95 (1H, m), 5.70-5.80 (1H, m), 7.55-7.95 (3H, m), 8.13-8.29 (1H, m), 8.48-8.61 (1H, m).

Workup

  1. stirringThe mixture stirred at room temperature for 4 hr
  2. washwashed with saturated aq. NaHCO3, saturated aq. NaCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (67% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4df429fe8eda4732a191c584b5a4b05c
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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