N,N'-Dimethylethylenediamine → HCID 11442583, compound

HRID 2217844Notes

Reaction equation

HRID 2217844 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8]([C:12]([NH:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:13])=[C:7]([Cl:22])[CH:6]=[CH:5][C:4]=2[N:3]=1.[CH3:23][NH:24][CH2:25][CH2:26][NH:27][CH3:28]>C(#N)C>[ClH:1].[ClH:1].[Cl:22][C:7]1[CH:6]=[CH:5][C:4]2[N:3]=[C:2]([N:24]([CH3:23])[CH2:25][CH2:26][NH:27][CH3:28])[CH:11]=[CH:10][C:9]=2[C:8]=1[C:12]([NH:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:13]

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 860130222,6-dichloro-N-(cyclohexylmethyl)-5-quinolinecarboxamide

Product 1

HCID 11442583HCID 11442583, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

A stirred suspension of 2,6-dichloro-N-(cyclohexylmethyl)quinoline-5-carboxamide (Example 43 (a)) (200 mg) and N,N′-dimethyl-1,2-ethanediamine (0.30 mL) in acetonitrile (2 mL) was heated at 100° C. in a microwave for 90 minutes after which it was cooled to room temperature and concentrated. Purification (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 95:5:0.5), conversion to the dihydrochloride salt by treatment with hydrochloric acid (4M in 1,4-dioxane) and recrystallisation (methanol/ethyl acetate) afforded the title compound as a solid (160 mg).

Workup

  1. temperaturewas cooled to room temperature
  2. concentrationconcentrated
  3. customPurification (SiO2, dichloromethane:methanol:ammonia in methanol (7 M) 95:5:0.5), conversion to the dihydrochloride salt by treatment
  4. customwith hydrochloric acid (4M in 1,4-dioxane) and recrystallisation (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-2e4a5ac1096e4f47947e596788ae87da
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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