HCID 69652414, compound → HCID 86592850, compound

HRID 2212209Notes

Reaction equation

HRID 2212209 reaction equation
C(OC([N:8]1[CH2:13][CH:12]([C:14](=[O:23])[NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:11][CH:10]([N:24]2[C:33]3[CH:32]=[CH:31][CH:30]=[C:29]([Cl:34])[C:28]=3[C:27]3=[N:35][O:36][C:37]([CH3:38])=[C:26]3[C:25]2=[O:39])[CH2:9]1)=O)(C)(C)C>Cl>[ClH:34].[ClH:34].[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][NH:15][C:14]([CH:12]2[CH2:11][CH:10]([N:24]3[C:33]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:34])[C:28]=4[C:27]4=[N:35][O:36][C:37]([CH3:38])=[C:26]4[C:25]3=[O:39])[CH2:9][NH:8][CH2:13]2)=[O:23])[CH:18]=1

Participants

3

Reactant 1

HCID 69652414HCID 69652414, compound

Product 1

HCID 86592850HCID 86592850, compoundYield 297.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Stir a solution of 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-5-[(pyridin-3-ylmethyl)-carbamoyl]-piperidine-1-carboxylic acid tert-butyl ester (30 mg, 0.05 mmol) in HCl-saturated HOAc (5 mL) 2 H at room temperature then concentrate to dryness. Dissolve 2× in toluene and concentrate to dryness to yield the title compound (26 mg, 100%) as a white oil as a mixture of cis isomers. MS(IS) 452.1 (M+); HPLC (5–95% (0.1% TFA/CH3CN) in (0.1% TFA/water) in 3.8 min on YMC ODS-A (0.46×50 mm) 5 μL/min; 25° C.) Rt=1.6 (min 100%).

Workup

  1. concentrationthen concentrate to dryness
  2. dissolutionDissolve 2× in toluene
  3. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-c40355f2e95b47f8927903682549f1c6
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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