Methylamine → HCID 23582858, compound

HRID 2242863Notes

Reaction equation

HRID 2242863 reaction equation
[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20]Cl)=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2.[CH3:22][NH2:23]>C(#N)C>[ClH:1].[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][NH:23][CH3:22])=[CH:13][CH:12]=2)[N:4]=[C:5]2[C:10]=1[CH:9]=[CH:8][CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 6329MethylamineHCID 58900128HCID 58900128, compound

Product 1

HCID 23582858HCID 23582858, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared from product from step 1 (0.6 g, 1.9 mmol) and methyl amine (40% in water, 16.2 mL, 0.47 mol) in acetonitrile (6 mL) was heated to 60° C. for 7 h, and then room temperature for 16 h. The mixture was extracted with ethyl acetate. The combined organic portions were acidified with 10% HCl to pH to 1, and stirred at 0° C. for 1 h. The product was collected on a filter, washed with 1N HCl, water and hexane. After drying under vacuum, the title compound (0.5 g, 79%)as a hydrochloride salt. 1H NMR (400 MHz, CD3OD) δ 7.66-7.60 (m, d, J=9.2 Hz, 4H), 7.43-7.39 (m, 1H), 7.23-7.18 (m, d, J=9.2 Hz, 3H), 4.24 (t, J=6 Hz, 2H), 3.27 (t, J=6 Hz, 2H), 2.77 (s, 3H), 2.24 (m, 2H); MS (APCI) m/z 316 (M+1, 100); LC/MS (APCI) m/z: 99%.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe product was collected on a filter
  3. washwashed with 1N HCl, water and hexane
  4. customAfter drying under vacuum

Sources & evidence

ORD record
ord-ce10cbf697744158a57e7ac630133eb4
Source dataset
uspto-grants-2010_03
Patent number
US07674802B2

Reaction notes

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