HCID 68546409, compound → HCID 68653320, compound

HRID 2243844Notes

Reaction equation

HRID 2243844 reaction equation
[N+](C1N=C2N(C=1)CC(OCC1C=CC(OCC(N3CCC(=O)CC3)=O)=CC=1)CO2)([O-])=O.C([O:36][C:37](=[O:60])[CH2:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([CH2:46][O:47][CH:48]2[CH2:53][O:52][C:51]3=[N:54][C:55]([N+:57]([O-:59])=[O:58])=[CH:56][N:50]3[CH2:49]2)=[CH:42][CH:41]=1)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[N+:57]([C:55]1[N:54]=[C:51]2[N:50]([CH:56]=1)[CH2:49][CH:48]([O:47][CH2:46][C:43]1[CH:42]=[CH:41][C:40]([O:39][CH2:38][C:37]([OH:60])=[O:36])=[CH:45][CH:44]=1)[CH2:53][O:52]2)([O-:59])=[O:58]

Participants

5

Reactant 2

HCID 68546409HCID 68546409, compoundHCID 68654235HCID 68654235, compound

Product 1

HCID 68653320HCID 68653320, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1-{2-[4-(2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-phenoxy]-acetyl}-piperidin-4-one. A solution of [4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxylmethyl)-phenoxy]-acetic acid tert-butyl ester (130 mg, 0.32 mmol) in TFA (1.0 mL) and dichloromethane (2.0 mL) was stirred at room temperature for 1.5 h. Solvent was evaporated to give [4-(2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-yloxymethyl)-phenoxy]-acetic acid. To a solution of the above acid in dichloromethane (6.0 mL) under N2 was added diisopropylethylamine (0.20 mL), 4-piperidone hydrochloride monohydrate (98 mg, 0.64 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (80 mg, 0.42 mmol), 1-hydrobenzotriazole (52 mg, 0.38 mmol). The mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with dichloromethane, washed with saturated NaHCO3 and 1 N HCl solution, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by preparative TLC plates (5% MeOH in dichloromethane) to give the title product as oil (28.0 mg, 20%). ESI MS m/z 431 (M+H+); 1H NMR (400 MHz, CDCl3) δ 7.37 (s, 1H), 7.26 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 4.77 (s, 2H), 4.67-4.53 (m, 3H), 4.32 (d, J=12.0 Hz, 1H), 4.15-4.07 (m, 3H), 3.91-3.85 (m, 4H), 2.50-2.45 (m, 4H).

Workup

  1. customSolvent was evaporated

Sources & evidence

ORD record
ord-425c9d637a9c405ea805969fe38549c1
Source dataset
uspto-grants-2010_03
Patent number
US07678791B2

Reaction notes

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