Hydrochloric Acid → 1-(2-Chloro-phenyl)-3-{6-[4-(3-morpholin-4-yl-propoxy)-phenylamino]-pyrimidin-4-yl}-urea

HRID 1038702Notes

Reaction equation

HRID 1038702 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1)=[O:10].[N:19]1([CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][CH:30]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.Cl>C(O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[C:16]([NH:35][C:32]2[CH:33]=[CH:34][C:29]([O:28][CH2:27][CH2:26][CH2:25][N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[CH:30][CH:31]=2)[N:15]=[CH:14][N:13]=1)=[O:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 220609034-(3-Morpholinopropoxy)anilineHCID 860869821-(2-Chloro-phenyl)-3-(6-chloro-pyrimidin-4-yl)-urea

Product 1

HCID 577102331-(2-Chloro-phenyl)-3-{6-[4-(3-morpholin-4-yl-propoxy)-phenylamino]-pyrimidin-4-yl}-urea

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(2-chloro-phenyl)-3-(6-chloro-pyrimidin-4-yl)-urea (99 mg, 0.35 mmol), 4-(3-morpholin-4-yl-propoxy)-phenylamine [Chabrier et al. Bull. Soc. Chim. Fr. 1955; 1353] (83 mg, 0.35 mmol), and concentrated HCl (0.1 ml, 1.4 mmol) in ethanol (5 ml) was refluxed for 32 h. The reaction mixture is cooled to RT, and diluted with water. The acidic solution is washed with ethyl acetate, basified with aqueous ammoniac, and extracted with DCM. The combined organic phases are dried over sodium sulfate, evaporated in vacuo, the residue is crystallized from water/methanol/1 N HCl to afford the title compound.

Workup

  1. washThe acidic solution is washed with ethyl acetate
  2. extractionextracted with DCM
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customevaporated in vacuo
  5. customthe residue is crystallized from water/methanol/1 N HCl

Sources & evidence

ORD record
ord-e2cc3a53924d430daf9f9ea2783398f2
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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