Potassium Carbonate → HCID 54692316, compound

HRID 1162836Notes

Reaction equation

HRID 1162836 reaction equation
C([O:4][C:5]1[C:10](=[O:11])[N:9]([CH:12]([CH3:14])[CH3:13])[C:8](=[O:15])[N:7]2[CH:16]([CH2:29][CH2:30][N:31]([C:33](=[O:35])[CH3:34])[CH3:32])[CH2:17][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[C:19](=[O:20])[C:6]=12)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[F:28][C:25]1[CH:24]=[CH:23][C:22]([CH2:21][N:18]2[CH2:17][CH:16]([CH2:29][CH2:30][N:31]([CH3:32])[C:33](=[O:35])[CH3:34])[N:7]3[C:8](=[O:15])[N:9]([CH:12]([CH3:14])[CH3:13])[C:10](=[O:11])[C:5]([OH:4])=[C:6]3[C:19]2=[O:20])=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68430205HCID 68430205, compound

Product 1

HCID 54692316HCID 54692316, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-{2-[acetyl(methyl)amino]ethyl}-2-(4-fluorobenzyl)-7-isopropyl-1,6,8-trioxo-1,3,4,6,7,8-hexahydro-2H-pyrazino[1,2-c]pyrimidine-9-yl acetate (28 mg, 0.057 mmol) in MeOH (2 mL) at ambient temperature under inert atmosphere was added potassium carbonate (48 mg, 0.344 mmol). After 1.5 h, the solvent was removed in vacuo and the residue treated with 1 N aqueous HCl solution and MeOH. The solvent was again removed in vacuo and the residue suspended in CH2Cl2. The mixture was filtered through a cotton plug, and the filtrate was concentrated in vacuo to give an orange oil. Purification by reverse phase chromatography [95:5 water (+0.1% TFA)/MeCN (+0.1% TFA) to 5:95 water (+0.1% TFA)/MeCN (+0.1% TFA)] afforded the title compound as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 11.76 (br s, 1H), 7.39-7.36 (m, 2H), 7.09-7.05 (m, 2H), 5.16 (dt, J=6.8, 13.6 Hz, 1H), 4.97 (d, J=14.0 Hz, 1H), 4.43 (d, J=11.2 Hz, 1H), 4.35 (d, J=14.4 Hz, 1H), 3.84 (br s, 1H), 1.77-1.70 (m, 1H), 1.46 (dd, J=1.6, 6.8 Hz, 6H). HRMS (FT/ES) M+H: calcd for (C22H27FN4O5)+ 447.2038. found 447.2031.

Workup

  1. customthe solvent was removed in vacuo
  2. additionthe residue treated with 1 N aqueous HCl solution and MeOH
  3. customThe solvent was again removed in vacuo
  4. filtrationThe mixture was filtered through a cotton plug
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto give an orange oil
  7. customPurification by reverse phase chromatography [95:5 water (+0.1% TFA)/MeCN (+0.1% TFA) to 5:95 water (+0.1% TFA)/MeCN (+0.1% TFA)]

Sources & evidence

ORD record
ord-5f4033a90c97436f872f925e83807d2c
Source dataset
uspto-grants-2010_10
Patent number
US07820680B2

Reaction notes

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