Trifluoroacetic acid → HCID 23081417, compound

HRID 856360Notes

Reaction equation

HRID 856360 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[N:16]([CH2:23][C:24]3([CH3:35])[O:28][C:27]4=[N:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][N:26]4[CH2:25]3)[C:15]2=[O:36])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:35][C:24]1([CH2:23][N:16]2[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15]2=[O:36])[O:28][C:27]2=[N:29][C:30]([N+:32]([O-:34])=[O:33])=[CH:31][N:26]2[CH2:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23081606HCID 23081606, compound

Product 1

HCID 23081417HCID 23081417, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(1-tert-butoxycarbonyl-piperidin-4-yl)-3-(2-methyl-6-nitro-2,3-dihydroimidazo-[2,1-b]oxazol-2-ylmethyl)-1,3-dihydrobenzimidazol-2-one prepared in Example 567 (371 mg, 0.74 mmol), trifluoroacetic acid (1 ml) and methylene chloride (10 ml) was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue, a saturated sodium hydrogencarbonate solution, and the precipitates were filtered off. The precipitates were washed with water several times to afford 1-(2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl)-(3-piperidin-4-yl)-1,3-dihydrobenzimidazol-2-one (255 mg, yield 86%) as a light yellow powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationTo the residue, a saturated sodium hydrogencarbonate solution, and the precipitates were filtered off
  3. washThe precipitates were washed with water several times

Sources & evidence

ORD record
ord-4bcadddbe70845b5aef42d8d73a53bdd
Source dataset
uspto-grants-2007_08
Patent number
US07262212B2

Reaction notes

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