Diisopropylethylamine → (E)-6-(3-(3-(3-Methylbenzofuran-2-yl)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 634035Notes

Reaction equation

HRID 634035 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.[O:17]=[C:18]1[NH:27][C:26]2[N:25]=[CH:24][C:23](/[CH:28]=[CH:29]/[C:30](O)=[O:31])=[CH:22][C:21]=2[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>[CH3:2][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[CH2:13][N:14]([C:30](=[O:31])/[CH:29]=[CH:28]/[C:23]2[CH:22]=[C:21]3[C:26](=[N:25][CH:24]=2)[NH:27][C:18](=[O:17])[CH2:19][CH2:20]3)[CH2:15]1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid HydrochlorideHCID 67154696HCID 67154696, compound

Product 1

HCID 52950833(E)-6-(3-(3-(3-Methylbenzofuran-2-yl)azetidin-1-yl)-3-oxoprop-1-enyl)-3,4-dihydro-1,8-naphthyridin-2(1H)-oneYield 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3-methylbenzofuran-2-yl)azetidine hydrochloride (19.9 mg, 0.089 mmol) in DMF (2 mL) were added (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (15.8 mg, 0.062 mmol), EDCI.HCl (19.9 mg, 0.104 mmol), HOAt (14.0 mg, 0.103 mmol) and N,N-diisopropylethylamine (58 μL, 0.339 mmol). The reaction was stirred at rt for 21 h, after which the mixture was partitioned between EtOAc and H2O. The layers were separated and the aqueous layer extracted with EtOAc. The combined organic layers were washed with brine (3×), dried with Na2SO4 and concentrated. The residue was triturated twice with Et2O and the dried to yield (the title compound (14.0 mg, 58%) as a pale orange solid.

Workup

  1. customafter which the mixture was partitioned between EtOAc and H2O
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with EtOAc
  4. washThe combined organic layers were washed with brine (3×)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated
  7. customThe residue was triturated twice with Et2O
  8. customthe dried

Sources & evidence

ORD record
ord-86dd9253e46e420da3609835b8661f93
Source dataset
uspto-grants-2016_04
Patent number
US09321769B2

Reaction notes

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