Sodium Hydroxide → HCID 86709408, compound

HRID 2172274Notes

Reaction equation

HRID 2172274 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C@H:8]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2].[F:27][C:28]([F:45])([F:44])[C:29]1[CH:30]=[CH:31][C:32]([O:35][C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)=[N:33][CH:34]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CN1CCCC1=O>[N+:1]([C:4]1[N:5]=[C:6]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C@H:8]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][N:24]([CH2:40][C:39]4[CH:38]=[CH:37][C:36]([O:35][C:32]5[CH:31]=[CH:30][C:29]([C:28]([F:45])([F:27])[F:44])=[CH:34][N:33]=5)=[CH:43][CH:42]=4)[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 269857004-{[5-(Trifluoromethyl)pyridin-2-yl]oxy}benzaldehydeHCID 70874384HCID 70874384, compound

Product 1

HCID 86709408HCID 86709408, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(R)-2-Nitro-7-(4-piperazin-1-ylphenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.50 g), 4-(5-trifluoromethylpyridin-2-yloxy)benzaldehyde (0.41 g), N-methylpyrrolidone (10 ml), and sodium triacetoxyborohydride (0.44 g) were mixed and stirred at room temperature for 16 hours. The reaction mixture was added to a 1 N sodium hydroxide aqueous solution. The precipitated crystal was collected by filtration. The crude crystal was purified by silica gel column chromatography (methylene chloride:ethyl acetate=8:2→methylene chloride:ethyl acetate=2:8) and recrystallized from acetone-ether to afford the title compound as a pale yellow powder (0.55 g).

Workup

  1. filtrationThe precipitated crystal was collected by filtration
  2. customThe crude crystal was purified by silica gel column chromatography (methylene chloride:ethyl acetate=8:2→methylene chloride:ethyl acetate=2:8)
  3. customrecrystallized from acetone-ether

Sources & evidence

ORD record
ord-941b05dcb43b43f6a3373ae733c8b9d0
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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