Acetic Acid → HCID 71610558, compound

HRID 1399799Notes

Reaction equation

HRID 1399799 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([NH:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:10]([NH2:25])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[CH3:26][C:27](O)=O>>[CH3:26][C:27]1[N:13]([CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)[C:11]2=[N:12][C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)=[CH:8][CH:9]=[C:10]2[N:25]=1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 89647472HCID 89647472, compound

Product 1

HCID 71610558HCID 71610558, compoundYield 14%

Procedure

A mixture of 6-morpholino-N2-(naphthalen-1-ylmethyl)pyridine-2,3-diamine (3.2 g, 9.58 mmol) in CH3COOH (50 mL) was refluxed for 16 h. The mixture was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography eluted with EtOAc/Pet Ether=1/1 and then recrystallized in EtOAc to afford the desired product as a pale solid (481 mg, 14%); LC/MS: MS (ES+) m/e 359 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 2.36 (s, 3H), 3.39 (t, J=4.8 Hz, 4H), 3.67 (t, J=4.8 Hz, 4H), 5.87 (s, 2H), 6.72-6.77 (m, 2H), 7.37-7.42 (m, 1H), 7.56-7.65 (m, 2H), 7.80 (d, J=8.7 Hz, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.98-8.01 (m, 1H), 8.36-8.39 (m, 1H).

Workup

  1. temperaturewas refluxed for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography
  4. washeluted with EtOAc/Pet Ether=1/1
  5. customrecrystallized in EtOAc

Sources & evidence

ORD record
ord-ab5d14ec84294b369d5b3883a3e992ca
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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