HCID 22036346, compound → HCID 22036240, compound

HRID 1789770Notes

Reaction equation

HRID 1789770 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[O:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([N:19]2[CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)=[N:15][CH:16]=[CH:17][N:18]=1>CCOC(C)=O.CCOCC.Cl.CCOCC>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:32]=[CH:33][CH:34]=1)[O:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:15][CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 1

HCID 22036346HCID 22036346, compound

Product 1

HCID 22036240HCID 22036240, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolventHCID 10953452Ether hydrochlorideSolvent

Procedure

The product obtained in Step 1 above was dissolved in a mixture of EtOAc (18 mL) and ether (9 mL) and 5 M HCl/ether (9 mL) was added. The mixture was stirred at room temperature for 3 h. The precipitated hydrochloride salt was filtered off and washed thoroughly with ether. The hydrochloride was dissolved in EtOAc/MeOH/Et3N (100:40:5) and purified by column chromatography) on silica using NH3-satd. EtOAc/CH3OH (100:15) as eluent. The combined pure fractions were concentrated in vacuo and the resulting oil was dried (˜0.8 torr, room temperature) to give 0.36 g (69%) of the title product. HRMS m/z calcd for C19H26N4O4 (M)+374.1954, found 374.1947.

Workup

  1. additionwas added
  2. filtrationThe precipitated hydrochloride salt was filtered off
  3. washwashed thoroughly with ether
  4. dissolutionThe hydrochloride was dissolved in EtOAc/MeOH/Et3N (100:40:5)
  5. custompurified by column chromatography) on silica
  6. concentrationThe combined pure fractions were concentrated in vacuo
  7. customthe resulting oil was dried (˜0.8 torr, room temperature)

Sources & evidence

ORD record
ord-87f51bec0164419d94ede3554fb73ac6
Source dataset
uspto-grants-2006_07
Patent number
US07071180B2

Reaction notes

Loading…