Dichloromethane → HCID 70866055, compound

HRID 2039967Notes

Reaction equation

HRID 2039967 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]2[CH:15]=[C:14]([CH2:16][OH:17])[NH:13][C:10]2=[N:11][CH:12]=1)=[O:5].ClCCl.[N:25]1[C:34]2[C:29](=[CH:30][C:31]([C:35](Cl)=[O:36])=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(OCC)(=O)C>[N:25]1[C:34]2[C:29](=[CH:30][C:31]([C:35]([O:17][CH2:16][C:14]3[NH:13][C:10]4=[N:11][CH:12]=[C:7]([NH:6][C:4](=[O:5])[C:3]5[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=5[Br:1])[CH:8]=[C:9]4[CH:15]=3)=[O:36])=[CH:32][CH:33]=2)[N:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2776328Quinoxaline-6-carbonyl chlorideHCID 49766392HCID 49766392, compound

Product 1

HCID 70866055HCID 70866055, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A flask is charged successively with 50 mg (0.14 mmol) of 2-bromo-N-(2-(hydroxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzamide AT2-2BF2 (example 16), 5 mL of dichloromethane, 30 mg (0.15 mmol) of 6-quinoxalinecarbonyl chloride and 30 μL (0.22 mmol) of triethylamine. The solution is stirred at room temperature for 18 hours and then diluted in 60 mL of ethyl acetate, washed with 10 mL of saturated solution of sodium bicarbonate, 10 mL of water, and 10 mL of saturated solution of sodium chloride. The organic phase is then dried over sodium sulphate and evaporated under reduced pressure. The raw product is then purified by silica gel chromatography (ethyl acetate/petroleum ether eluent). 14 mg of a yellow solid is obtained (24%).

Workup

  1. washwashed with 10 mL of saturated solution of sodium bicarbonate, 10 mL of water, and 10 mL of saturated solution of sodium chloride
  2. dry with materialThe organic phase is then dried over sodium sulphate
  3. customevaporated under reduced pressure
  4. customThe raw product is then purified by silica gel chromatography (ethyl acetate/petroleum ether eluent)

Sources & evidence

ORD record
ord-a43c4cb1ddcc420397dd94a2091993ec
Source dataset
uspto-grants-2013_11
Patent number
US08580815B2

Reaction notes

Loading…