Diethylamine → HCID 15982174, compound

HRID 2220493Notes

Reaction equation

HRID 2220493 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[CH2:7][N:6]([CH3:20])[CH2:5][C:4]=2[N:3]=1.N(CC)CC.[CH2:26]([N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[CH2:27][C:28]#[CH:29].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH:8]2[CH2:7][N:6]([CH3:20])[CH2:5][C:4]3[N:3]=[C:2]([C:29]#[C:28][CH2:27][CH2:26][N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:11]=[CH:10][C:9]2=3)=[CH:13][CH:14]=1

Participants

8

Reactant 4

HCID 8021DiethylamineHCID 11776TriphenylphosphineHCID 131559861-(But-3-yn-1-yl)piperidineHCID 58771901HCID 58771901, compound

Product 1

HCID 15982174HCID 15982174, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A flask containing a mixture of 2-chloro-5-(4-methoxy-phenyl)-7-methyl-5,6,7,8-tetrahydro-[1,7]naphthyridine (0.080 g, 0.28 mmol), Et2NH (1.0 mL), 1-but-3-ynyl-piperidine (0.077 g, 0.56 mmol), CuI (5.3 mg, 27.8 umol), PPh3 (36 mg, 0.14 mmol), and Pd(PPh3)2Cl2 (0.020 g, 0.028 mmol) in DMF (0.5 mL) was evacuated and back-filled with N2 (3×). The mixture was heated at 105 C for 18 h, then was cooled to rt, diluted with satd. aq. NaHCO3, and extracted with DCM. The combined organic layers were washed with H2O, dried, and concentrated. The residue was purified (SiO2; 0-6% 2 M NH3 in MeOH/DCM) to give the title compound (35 mg, 33%). MS (ESI): mass calcd. for C25H31N3O, 389.25; m/z found, 390.6 [M+H]+. 1H NMR (CDCl3): 7.15-7.08 (m, 2H), 7.06 (d, J=8.7, 2H), 6.83 (d, J=8.7, 2H), 4.23-4.17 (m, 1H), 3.91-3.85 (m, 1H), 3.79 (s, 3H), 3.66-3.59 (m, 1H), 3.05-2.99 (m, 1H), 2.76-2.62 (m, 4H), 2.56-2.46 (m, 5H), 2.45 (s, 3H), 1.68-1.58 (m, 4H), 1.49-1.40 (m, 2H).

Workup

  1. additionA flask containing
  2. customwas evacuated
  3. additionback-filled with N2 (3×)
  4. temperatureThe mixture was heated at 105 C for 18 h
  5. additiondiluted with satd
  6. extractionaq. NaHCO3, and extracted with DCM
  7. washThe combined organic layers were washed with H2O
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified (SiO2; 0-6% 2 M NH3 in MeOH/DCM)

Sources & evidence

ORD record
ord-fcd96612934f475ba2d815419f31c289
Source dataset
uspto-grants-2008_08
Patent number
US07417054B2

Reaction notes

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