Potassium Carbonate → HCID 131730960, compound

HRID 2035500Notes

Reaction equation

HRID 2035500 reaction equation
[F:1][C:2]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)[N:9]=[CH:8][C:7]=1[CH2:25][C:26]([NH2:28])=[O:27].Br.Br[CH2:36][CH2:37][N:38]([CH2:41][CH3:42])[CH2:39][CH3:40].C(=O)([O-])[O-].[K+].[K+].C(N(CC)C=O)C>>[CH2:37]([N:38]([CH2:41][CH3:42])[CH2:39][CH2:40][N:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]3[N:9]=[CH:8][C:7]([CH2:25][C:26]([NH2:28])=[O:27])=[C:6]([NH:5][CH2:4][C:3]4[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:2]=4[F:1])[CH:11]=3)=[CH:14][CH:15]=2)[CH2:24][CH2:23]1)[CH3:36]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 12051DiethylformamideHCID 706072-Bromoethyldiethylammonium bromideHCID 131730961HCID 131730961, compound

Product 1

HCID 131730960HCID 131730960, compoundYield 60%

Conditions

Temperature
70 °C

Procedure

120 mg of 4-[(2,3-difluorobenzyl)amino]-6-{[4-(piperazin-1-yl)phenyl]amino}pyridine-3-carboxyamide (the compound of Example 220), 72 mg of 2-bromoethyl-N,N-diethylamine.hydrobromide and 72 mg of potassium carbonate were added to 2 mL of N,N-diethylformamide, and stirred at 70° C. for 1.5 hour. The solvent was evaporated, and the residue was dissolved in chloroform, washed with saturated saline, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1) to obtain 74 mg (60%) of the title compound as a light brown powder.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washwashed with saturated saline
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:ammonia methanol=10:1)

Sources & evidence

ORD record
ord-deccebba8f694a86a59b323110456b13
Source dataset
uspto-grants-2013_11
Patent number
US08575153B2

Reaction notes

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