Sodium Carbonate → HCID 15817416, compound

HRID 1977049Notes

Reaction equation

HRID 1977049 reaction equation
Cl.Cl.[CH2:3]1[NH:8][CH2:7][CH2:6][N:5]2[CH2:9][C@H:10]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][C:15]3=[O:23])[CH2:11][CH2:12][C@@H:4]12.Cl[C:25]1[N:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[N:26]1[CH:27]=[CH:28][CH:29]=[N:30][C:25]=1[N:8]1[CH2:7][CH2:6][N:5]2[CH2:9][C@H:10]([CH2:13][N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH2:16][C:15]3=[O:23])[CH2:11][CH2:12][C@H:4]2[CH2:3]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 69430557HCID 69430557, compound

Product 1

HCID 15817416HCID 15817416, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 0.49 g (1.38 mmol) of 1-[(7R,9aS)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazin-7-ylmethyl]-1,3-dihydro-indol-2-one dihydrochloride, 0.157 g (1.37 mmol) of 2-chloropyrimidine and 0.64 g (6.02 mmol) of sodium carbonate in 20 mL of water was stirred at 95° C. for 16 h. The mixture was cooled to room temperature, extracted with chloroform (3×), the combined organic phase was washed with brine, dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with 95:5 ethyl acetate:methanol gave 0.181 g (30%) of the title compound. mp (—HCl) 174-176° C. HRMS calcd for C21H25N5O: 363.2059, found: 363.2032.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with chloroform (3×)
  3. washthe combined organic phase was washed with brine
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with 95:5 ethyl acetate

Sources & evidence

ORD record
ord-3cddaac41206445781dc820c47b6f2a3
Source dataset
uspto-grants-2001_05
Patent number
US06231833B1

Reaction notes

Loading…