Triethylamine → N-[6-Chloro-2-[methyl[3-(methylamino)propyl]amino]-5-quinolinyl]-cyclohexanepropanamide

HRID 2217896Notes

Reaction equation

HRID 2217896 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:23])[C:8]=2[NH:12][C:13](=[O:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[N:3]=1.CN[CH:26]([NH:29][CH3:30])[CH2:27][CH3:28].[CH2:31]([N:33](CC)CC)C>>[Cl:23][C:7]1[C:8]([NH:12][C:13](=[O:22])[CH2:14][CH2:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([N:33]([CH3:31])[CH2:28][CH2:27][CH2:26][NH:29][CH3:30])[CH:11]=[CH:10]2

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 22287041HCID 22287041, compoundHCID 86012849N-(2,6-Dichloro-5-quinolinyl)-cyclohexanepropanamide

Product 1

HCID 11316027N-[6-Chloro-2-[methyl[3-(methylamino)propyl]amino]-5-quinolinyl]-cyclohexanepropanamide

Procedure

Prepared according to the method of example 90(b), using N-(2,6-dichloro-5-quinolinyl)-cyclohexanepropanamide (Example 90(a)) (0.16 g), N,N′-dimethylpropanediamine (0.3 mL) and triethylamine (0.1 mL). Purification (SiO2, methanol:dichloromethane:triethylamine 5:95:0.5 followed by HPLC, Symmetry—0.1% aqueous trifluoroacetic acid:acetonitrile) gave the title compound as a solid (70 mg).

Workup

  1. customPrepared
  2. customPurification (SiO2, methanol:dichloromethane:triethylamine 5:95:0.5 followed by HPLC, Symmetry—0.1% aqueous trifluoroacetic acid:acetonitrile)

Sources & evidence

ORD record
ord-bfdd404acf8a4e6796974f4fffa2f1e9
Source dataset
uspto-grants-2008_08
Patent number
US07408065B2

Reaction notes

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