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

HRID 1864048
Notes
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Reaction equation

HRID 1864048 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([N:13]([CH3:15])C)=[O:12])[C:5]([Cl:20])=[CH:4][N:3]=1.[N:21]1([CH2:27][CH2:28][C:29]2[CH:30]=[C:31]([CH:33]=[CH:34][CH:35]=2)[NH2:32])[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.Cl>C(O)(C)C>[Cl:20][C:5]1[C:6]([NH:8][C:9]2[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=2[C:11]([NH:13][C:15]2[CH:33]=[CH:34][CH:35]=[C:29]([CH2:28][CH2:27][N:21]3[CH2:22][CH2:23][O:24][CH2:25][CH2:26]3)[CH:30]=2)=[O:12])=[N:7][C:2]([NH:32][C:31]2[CH:33]=[CH:34][CH:35]=[C:29]([CH2:28][CH2:27][N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[CH:30]=2)=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 230715613-(Morpholinoethyl)anilineHCID 579741612-[(2,5-dichloropyrimidin-4-yl)amino]-N,N-dimethylbenzamide

Product 1

HCID 579741892-{[5-Chloro-2-({3-[2-(4-morpholinyl)ethyl]phenyl}amino)-4-pyrimidinyl]amino}-N-{3-[2-(4-morpholinyl)ethyl]phenyl}benzamideYield 9.7%

Reagents, catalysts & solvents 1

HCID 3776
Isopropanol
Solvent

Conditions

Temperature
95 °C

Procedure

2-[(2,5-Dichloro-4-pyrimidinyl)amino]-N,N-dimethylbenzamide (250 mg, 0.80 mmol), and 3-[2-(4-morpholinyl)ethyl]aniline (165 mg, 0.80 mmol) were combined in a vessel with 10 mL of isopropanol and 12N HCl (67 μL, 0.80 mmol). The vessel was sealed and heated with stirring at 95° C. for 18 h. The reaction mixture was concentrated to dryness. The crude product was purified by HPLC to afford the title compound as a white solid (25 mg, 6%): Mass (M+H)+=642, 644.

Workup

  1. customThe vessel was sealed
  2. temperatureheated
  3. concentrationThe reaction mixture was concentrated to dryness
  4. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-562b495b5063446c88fd577f9fbd05ae
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07625903B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes