Hydrochloric Acid → HCID 46174697, compound

HRID 1916052Notes

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

Participants

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

temperatureto cool down to room temperature
extractionextracted with ethyl acetate
washThe combined organic phases were washed with brine
dry with materialdried over sodium sulphate
filtrationfiltrated
concentrationconcentrated in vacuo
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

Loading…