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Acetic Acid → HCID 70873377, compound

HRID 2172258
Notes
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Reaction equation

HRID 2172258 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][C:24](=O)[CH2:23][CH2:22]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2].[F:28][C:29]([F:46])([F:45])[O:30][C:31]1[CH:44]=[CH:43][C:34]([O:35][C:36]2[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=2)=[CH:33][CH:32]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.O1CCCC1>[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[CH2:22][CH2:23][CH:24]([NH:42][C:39]4[CH:40]=[CH:41][C:36]([O:35][C:34]5[CH:43]=[CH:44][C:31]([O:30][C:29]([F:28])([F:45])[F:46])=[CH:32][CH:33]=5)=[CH:37][CH:38]=4)[CH2:25][CH2:26]3)=[CH:17][CH:16]=1)[O:7]2)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 116661924-(4-(Trifluoromethoxy)phenoxy)anilineHCID 70874615HCID 70874615, compound

Product 1

HCID 70873377HCID 70873377, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 11
1,2-Dichloroethane
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

1-[4-((R)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-one (700 mg) and 4-(4-trifluoromethoxyphenoxy)phenylamine (557 mg) were suspended in 1,2-dichloroethane (20 ml) and tetrahydrofuran (20 ml). Sodium triacetoxyborohydride (558 mg) and acetic acid (0.13 ml) were added to the suspension, and stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure and the remaining water layer was ice-cooled. A 20% sodium carbonate aqueous solution was added thereto, followed by extraction with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was then purified by silica gel column chromatography (methylene chloride:methanol=100:1→methylene chloride:methanol=40:1) and recrystallized from isopropyl alcohol-isopropyl ether to afford the title compound as a yellow solid (226 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperaturecooled
  3. additionA 20% sodium carbonate aqueous solution was added
  4. extractionfollowed by extraction with methylene chloride
  5. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtering
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was then purified by silica gel column chromatography (methylene chloride:methanol=100:1→methylene chloride:methanol=40:1)
  10. customrecrystallized from isopropyl alcohol-isopropyl ether

Sources & evidence

ORD record
ord-2eefdb16d8a042d39c2e6f2b7b23aa06
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051333B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes