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Hydrochloric Acid → HCID 46174697, compound

HRID 1916052
Notes
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Reaction equation

HRID 1916052 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]2)[N:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1.Cl>CN1CCCC1=O>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([NH:15][C:4]2[CH:3]=[C:2]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:7]=[C:6]([N:8]3[C:12]([CH3:13])=[CH:11][C:10]([CH3:14])=[N:9]3)[N:5]=2)=[CH:17][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 58442371HCID 58442371, compound

Product 1

HCID 46174697HCID 46174697, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of [6-chloro-2-(3,5-dimethyl-pyrazol-1-yl)-pyrimidin-4-yl]-(4-chlorophenyl)-amine (125 mg, 0.37 mmol) and morpholine (0.32 mL, 3.74 mmol) in 1-methyl-2-pyrrolidinone (4 mL) was stirred for one hour at 110° C. The reaction mixture was allowed to cool down to room temperature, acidified with aqueous hydrochloric acid (1 M) and extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulphate, filtrated and concentrated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol as eluent) to give (4-chloro-phenyl)-[2-(3,5-dimethyl-pyrazol-1-yl)-6-morpholin-4-yl-pyrimidin-4-yl]-amine (92 mg, 64%) as a white solid. Mp. 186-187° C.

Workup

  1. temperatureto cool down to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (dichloromethane/methanol as eluent)

Sources & evidence

ORD record
ord-4666aea1fe624f179d93d37340b98503
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes