Hydrochloric Acid → HCID 136375757, compound

HRID 869264Notes

Reaction equation

HRID 869264 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[N:15]=[C:16](SC)[NH:17][C:18](=[O:23])[C:19]=1[C:20]([NH2:22])=[O:21])(=[O:6])=[O:5])([CH3:3])[CH3:2].[NH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1C(OC(C)(C)C)=O.CN1C(=O)CCC1.[ClH:48]>C(OCC)(=O)C.C(O)C>[ClH:48].[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[N:15]=[C:16]([NH:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]2)[NH:17][C:18](=[O:23])[C:19]=1[C:20]([NH2:22])=[O:21])(=[O:6])=[O:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylateHCID 136375769HCID 136375769, compound

Product 1

HCID 136375757HCID 136375757, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
180 °C

Procedure

A mixture of 4-{[2-(isopropylsulfonyl)phenyl]amino}-2-(methylsulfanyl)-6-oxo-1,6-dihydropyrimidine-5-carboxamide (Preparation Example 294) (200 mg), tert-butyl 2-(aminomethyl)piperidine-1-carboxylate (1.12 g) and NMP (1 mL) was heated at 180° C. for 10 minutes using a microwave reaction system. After cooling, the reaction liquid was diluted with ethyl acetate and washed with water and saturated aqueous sodium chloride. After drying over anhydrous magnesium sulfate, the solvent was distilled off, and the residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1) to give a white amorphous. To a mixture of the white amorphous, ethyl acetate (10 mL) and ethanol (5 mL), 4M hydrogen chloride in ethyl acetate (5 mL) was added under ice cooling and stirred at room temperature for 4 hours. The precipitated solid was collected by filtration and dried to give 4-{[2-(isopropylsulfonyl)phenyl]amino}-6-oxo-2-[(piperidin-2-ylmethyl)amino]-1,6-dihydropyrimidine-5-carboxamide hydrochloride (126 mg) as a white solid.

Workup

  1. customa microwave reaction system
  2. temperatureAfter cooling
  3. customthe reaction liquid
  4. washwashed with water and saturated aqueous sodium chloride
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customthe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 20:1)
  8. customto give a white amorphous
  9. additionwas added under ice cooling
  10. filtrationThe precipitated solid was collected by filtration
  11. customdried

Sources & evidence

ORD record
ord-f0d677551afc455da844442a2b7c4d25
Source dataset
uspto-grants-2015_03
Patent number
US08969336B2

Reaction notes

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