Hydrochloric Acid → 2-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-(2-hydroxyethyl)benzamide

HRID 1362870Notes

Reaction equation

HRID 1362870 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH2:14][CH2:15][OH:16])=[O:12])[C:5]([F:21])=[CH:4][N:3]=1.[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][C:30]2[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=2)[NH2:33])[CH2:24][CH2:23]1.Cl>C(O)(C)C>[F:21][C:5]1[C:6]([NH:8][C:9]2[CH:20]=[CH:19][CH:18]=[CH:17][C:10]=2[C:11]([NH:13][CH2:14][CH2:15][OH:16])=[O:12])=[N:7][C:2]([NH:33][C:32]2[CH:34]=[CH:35][CH:36]=[C:30]([CH2:29][CH2:28][N:25]3[CH2:24][CH2:23][O:22][CH2:27][CH2:26]3)[CH:31]=2)=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 230715613-(Morpholinoethyl)anilineHCID 579741542-[(2-Chloro-5-fluoro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide

Product 1

HCID 509437342-{[5-Fluoro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-(2-hydroxyethyl)benzamideYield 71.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

2-[(2-Chloro-5-fluoro-4-pyrimidinyl)amino]-N-(2-hydroxyethyl)benzamide (500 mg, 1.61 mmol) and 3-(morpholinoethyl)aniline (352 mg, 1.61 mmol) were combined in a tube with 30 mL isopropanol and 12N HCl (134 μL, 1.60 mmol). The vessel was sealed and heated with stirring at 90° C. for 18 h. The reaction was cooled to room temperature and the solid was filtered off and washed with isopropanol and ether to give 550 mg (71% yield) of a white solid as the HCl salt, LC/MS (M+H)+ 480, 481.

Workup

  1. customThe vessel was sealed
  2. temperatureheated
  3. temperatureThe reaction was cooled to room temperature
  4. filtrationthe solid was filtered off
  5. washwashed with isopropanol and ether

Sources & evidence

ORD record
ord-4bc1018ddf6b48b5ae08d1888b9ef913
Source dataset
uspto-grants-2011_02
Patent number
US07884098B2

Reaction notes

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