Hydrochloric Acid → HCID 54748165, compound

HRID 1893213Notes

Reaction equation

HRID 1893213 reaction equation
CS([O:5][C:6]1[C:28](=[O:29])[N:10]2[CH2:11][C@@H:12]([O:26][CH3:27])[CH2:13][CH2:14][C@@H:15]([N:16]([C:19](=[O:25])[C:20]([N:22]([CH3:24])[CH3:23])=[O:21])[CH2:17][CH3:18])[C:9]2=[N:8][C:7]=1[C:30]([NH:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)=[O:31])(=O)=O.[OH-].[Na+].Cl>CC(O)C>[CH2:17]([N:16]([C@@H:15]1[CH2:14][CH2:13][C@H:12]([O:26][CH3:27])[CH2:11][N:10]2[C:28](=[O:29])[C:6]([OH:5])=[C:7]([C:30]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)=[O:31])[N:8]=[C:9]12)[C:19](=[O:25])[C:20]([N:22]([CH3:23])[CH3:24])=[O:21])[CH3:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86640591HCID 86640591, compound

Product 1

HCID 54748165HCID 54748165, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of (7S,10R)-10-[[(dimethylamino)(oxo)acetyl](ethyl)amino]-2-{[(4-fluorobenzyl)amino]carbonyl}-7-methoxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-3-yl methanesulfonate (1 g, 1.72 mmol) in 2-propanol (17 mL) was added 2M NaOH (2.58 mL, 5.16 mmol). The resulting mixture was stirred at ambient temperature for 30 minutes, quenched with HCl (1M, 5.16 mL, 5.16 mmol), and extracted with EtOAc (3×). Three additional reactions on the same scale were performed in parallel. The combined organic layers from all four reactions were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by reverse phase HPLC (C18 Sunfire column) using a water/acetonitrile mobile phase gradient containing 0.5% TFA or by precipitation from water to provide N-ethyl-N-((7S,10R)-2-{[(4-fluorobenzyl)amino]carbonyl}-3-hydroxy-7-methoxy-4-oxo-4,6,7,8,9,10-hexahydropyrimido[1,2-a]azepin-10-yl)-N′,N′-dimethylethanediamide. LC-MS: 504.5 (M+1).

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers from all four reactions were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by reverse phase HPLC (C18 Sunfire column)
  6. additioncontaining 0.5% TFA
  7. customby precipitation from water

Sources & evidence

ORD record
ord-0e019f4df29440318a0f0f69a4e8127b
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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