Potassium Carbonate → HCID 135939598, compound

HRID 1927279Notes

Reaction equation

HRID 1927279 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:21]=[C:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1.Br[CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:21]=[C:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178642-BromoethyldimethylamineHCID 135939592HCID 135939592, compound

Product 1

HCID 135939598HCID 135939598, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of EXAMPLE 12 (0.04 g, 0.1 mmol) and (2-bromoethyl) dimethylamine (0.02 g, 0.1 mmol) in acetonitrile (1 mL) was treated with potassium carbonate (0.04 g, 0.3 mmol). The mixture was stirred overnight at 50° C. and filtered. The filtrate was concentrated and purified by flash chromatography on silica gel with 10% methanol/dichloromethane to provide the title compound. 1H NMR (DMSO-d6) δ 8.12-8.18 (m, 2H), 7.86-7.95 (m, 1H), 7.49 (t, J=7.6 Hz, 1H), 7.12-7.20 (m, 3H), 6.64 (s, 1H), 6.27 (s, 1H), 3.23-3.26 (m, 3H), 2.57-2.65 (m, 1H), 2.31 (s, 6H), 1.24 (s, 1H), 0.85 (s, 1H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. custompurified by flash chromatography on silica gel with 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-c9e2e956ea55449f9842fa92bd99dc38
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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