Hydrochloric Acid → 2-Amino-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]-2-phenylacetamide

HRID 352236Notes

Reaction equation

HRID 352236 reaction equation
C(OC(=O)[NH:7][CH:8]([C:15](=[O:39])[NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([N:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:33])[C:27]=3[C:26]3=[N:34][O:35][C:36]([CH3:37])=[C:25]3[C:24]2=[O:38])[CH2:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.Cl>C(O)(=O)C>[NH2:7][CH:8]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:15]([NH:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([N:23]2[C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:33])[C:27]=3[C:26]3=[N:34][O:35][C:36]([CH3:37])=[C:25]3[C:24]2=[O:38])[CH2:18]1)=[O:39]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69848144{[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester

Product 1

HCID 227137392-Amino-N-[3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)cyclohexyl]-2-phenylacetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

{[3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexylcarbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester (1.24 g; 2.2 mmol) was dissolved in excess, neat acetic acid saturated with HCl(g) (20 mL). After stirring 30 min at room temperature, the solution was concentrated to dryness by rotary evaporation. Acetic acid was removed from the resulting solid by consecutive dissolution in, and drying from, acetonitrile (thrice) and then diethyl ether (once). The solid was dissolved in 25% (v/v) isopropyl alcohol in chloroform, washed with saturated NaHCO3(aq), and dried by rotary evaporation to yield the desired product in 97% isolated yield.

Workup

  1. concentrationthe solution was concentrated to dryness by rotary evaporation
  2. customAcetic acid was removed from the resulting solid by consecutive dissolution in, and
  3. dry with materialdrying from, acetonitrile (thrice)
  4. dissolutionThe solid was dissolved in 25% (v/v) isopropyl alcohol in chloroform
  5. washwashed with saturated NaHCO3(aq)
  6. customdried by rotary evaporation

Sources & evidence

ORD record
ord-adc3eccee718488ca44746e865800b39
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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