Diisopropylethylamine → HCID 52950834, compound

HRID 83087Notes

Reaction equation

HRID 83087 reaction equation
Cl.[CH3:2][C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]1[CH2:15][NH:14][CH2:13]1.Cl.[CH3:17][N:18]1[CH2:23][CH2:22][C:21]2([CH2:32][C:31]3[C:26](=[N:27][CH:28]=[C:29](/[CH:33]=[CH:34]/[C:35](O)=[O:36])[CH:30]=3)[NH:25][C:24]2=[O:38])[CH2:20][CH2:19]1.CCN=C=NCCCN(C)C.Cl.C1C=NC2N(O)N=NC=2C=1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH3:17][N:18]1[CH2:19][CH2:20][C:21]2([CH2:32][C:31]3[C:26](=[N:27][CH:28]=[C:29](/[CH:33]=[CH:34]/[C:35]([N:14]4[CH2:13][CH:12]([C:4]5[O:5][C:6]6[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=6[C:3]=5[CH3:2])[CH2:15]4)=[O:36])[CH:30]=3)[NH:25][C:24]2=[O:38])[CH2:22][CH2:23]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67154626HCID 67154626, compoundHCID 67154696HCID 67154696, compound

Product 1

HCID 52950834HCID 52950834, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-methylbenzofuran-2-yl)azetidine hydrochloride (21.7 mg, 0.097 mmol) and (E)-3-(1′-methyl-2-oxo-2,4-dihydro-1H-spiro[[1,8]naphthyridine-3,4′-piperidine]-6-yl)acrylic acid hydrochloride (22.0 mg, 0.065 mmol) in DMF (3 mL) were added EDCI.HCl (18.9 mg, 0.099 mmol), HOAt (13.9 mg, 0.102 mmol) and N,N-diisopropylethylamine (57 μL, 0.333 mmol). The reaction was stirred at rt for 20 h., after which the mixture was partitioned between DCM and H2O. The layers were separated and the aqueous layer extracted with DCM (3×). The combined organic layers were washed with brine (3×), dried over Na2SO4 and concentrated and the residue was purified by flash chromatography (DCM/MeOH, 5%→20%). The product (10.6 mg, 35%) was obtained as a white powder.

Workup

  1. customafter which the mixture was partitioned between DCM and H2O
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with DCM (3×)
  4. washThe combined organic layers were washed with brine (3×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography (DCM/MeOH, 5%→20%)

Sources & evidence

ORD record
ord-ad95deb58f134f5892a47240aca3fed9
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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