Hydrochloric Acid → HCID 11527623, compound

HRID 1441281Notes

Reaction equation

HRID 1441281 reaction equation
[CH2:1]([N:3]([CH2:14][CH3:15])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)[CH3:2].Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)=[O:26])=[CH:20][C:19]=1[N:39]1[CH2:48][C:47]2[C:42](=[N:43][C:44](S(C)(=O)=O)=[N:45][CH:46]=2)[N:41]([CH3:53])[C:40]1=[O:54]>CN1CCCC1=O.C(OCC)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)=[CH:29][CH:28]=2)=[O:26])=[CH:20][C:19]=1[N:39]1[CH2:48][C:47]2[C:42](=[N:43][C:44]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:14][CH3:15])=[CH:12][CH:11]=3)=[N:45][CH:46]=2)[N:41]([CH3:53])[C:40]1=[O:54]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 11628130HCID 11628130, compound

Product 1

HCID 11527623HCID 11527623, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.1 g 4-(2-Diethylamino-ethoxy)-phenylamine were dissolved in 1 mL N-methylpyrrolidinone (NMP) and cooled to 0° C. 300 μl of a solution of aqueous HCl in diethyl ether were added and stirred for 45 min. Biphenyl-4-carboxylic acid [4-chloro-3-(7-methanesulfonyl-1-methyl-2-oxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-amide was dissolved in 2 ml NMP and added to the aforementioned solution and the reaction mixture was heated at 120° C. for 24 h. The reaction was quenched by addition of 5 mL of a saturated solution of sodium carbonate and the aqueous phase was extracted with dichloromethane. The organic phase was dried over sodium sulfate and the solvent was evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol) to give the title product in 35% yield.

Workup

  1. additionadded to the aforementioned solution
  2. temperaturethe reaction mixture was heated at 120° C. for 24 h
  3. customThe reaction was quenched by addition of 5 mL of a saturated solution of sodium carbonate
  4. extractionthe aqueous phase was extracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol)

Sources & evidence

ORD record
ord-6df35bdbe77a48d3875ba694e8a6156e
Source dataset
uspto-grants-2010_02
Patent number
US07655651B2

Reaction notes

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