Diisopropylethylamine → HCID 23377662, compound

HRID 1279266Notes

Reaction equation

HRID 1279266 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([NH2:9])[CH2:5][CH2:6][O:7][CH3:8].Cl[C:11]1[CH:16]=[C:15]([CH3:17])[NH:14][C:13](=[O:18])[C:12]=1[N+:19]([O-:21])=[O:20].C(N(C(C)C)CC)(C)C>CC#N.C(Cl)Cl>[CH3:17][C:15]1[NH:14][C:13](=[O:18])[C:12]([N+:19]([O-:21])=[O:20])=[C:11]([NH:9][C@H:4]([CH2:3][O:2][CH3:1])[CH2:5][CH2:6][O:7][CH3:8])[CH:16]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 114354124-CHLORO-6-METHYL-3-NITROPYRIDIN-2(1H)-ONEHCID 18629275HCID 18629275, compound

Product 1

HCID 23377662HCID 23377662, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

1-methoxymethyl-3-methoxypropylamine (4.19 g, 22.3 mmol), and 4-chloro-6-methyl-3-nitropyridone (3.87 g, 22.3 mmol) were mixed in CH3CN (70 mL) and diisopropyl-ethylamine (9.4 mL, 53.6 mmol) was added. The reaction was stirred at 25° C. for 16 h and at reflux for 2.5 h. The solvent was stripped off and the residue was dissolved in CH2Cl2 (150 mL) and the CH2Cl2 was washed with water (80 mL). The water was extracted with CH2Cl2 (50 mL) and the combined organic extracts were dried (MgSO4) and stripped in vacuo. The residue was crystallized from EtOAc and washed with 40% EtOAc/hexanes to give the product, (4.8 g, 75%). NMR(DMSO)d 9.13 (d, 1H, J=8.8 Hz), 5.9 (s, 1H), 3.92-4.02 (m, 1H), 3.20-3.25 (m, 2H), 3.28-3.4 (m, 2H), 3.25 (s, 3H), 3.18 (s, 3H), 2.09 (s, 3H), 1.65-1.90 (m, 2H).

Workup

  1. temperatureat reflux for 2.5 h
  2. washthe CH2Cl2 was washed with water (80 mL)
  3. extractionThe water was extracted with CH2Cl2 (50 mL)
  4. dry with materialthe combined organic extracts were dried (MgSO4)
  5. customThe residue was crystallized from EtOAc
  6. washwashed with 40% EtOAc/hexanes
  7. customto give the product, (4.8 g, 75%)

Sources & evidence

ORD record
ord-a9f71c85674a43459e11881bdacfdb52
Source dataset
uspto-grants-2002_09
Patent number
US06448261B1

Reaction notes

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