Acetic Acid → HCID 70874368, compound

HRID 2172260Notes

Reaction equation

HRID 2172260 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[N+:19]([C:22]1[N:23]=[C:24]2[N:29]([CH:30]=1)[CH2:28][CH2:27][C@H:26]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]3[CH2:44][CH2:43][C:42](=O)[CH2:41][CH2:40]3)=[CH:35][CH:34]=1)[O:25]2)([O-:21])=[O:20].[F:46][C:47]([F:65])([F:64])[O:48][C:49]1[CH:63]=[CH:62][C:52]([CH2:53][O:54][C:55]2[CH:60]=[CH:59][C:58]([NH2:61])=[CH:57][CH:56]=2)=[CH:51][CH:50]=1>C(Cl)Cl.ClCCCl>[N+:19]([C:22]1[N:23]=[C:24]2[N:29]([CH:30]=1)[CH2:28][CH2:27][C@H:26]([CH2:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([N:39]3[CH2:44][CH2:43][CH:42]([NH:61][C:58]4[CH:57]=[CH:56][C:55]([O:54][CH2:53][C:52]5[CH:62]=[CH:63][C:49]([O:48][C:47]([F:46])([F:64])[F:65])=[CH:50][CH:51]=5)=[CH:60][CH:59]=4)[CH2:41][CH2:40]3)=[CH:35][CH:34]=1)[O:25]2)([O-:21])=[O:20]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 18071081HCID 18071081, compoundHCID 70874615HCID 70874615, compound

Product 1

HCID 70874368HCID 70874368, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (0.32 g) and acetic acid (1 ml) were added to a 1,2-dichloroethane solution (8 ml) of 1-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-one (0.40 g) and 4-(4-trifluoromethoxybenzyloxy)phenylamine (0.33 g), and the mixture was stirred at room temperature for 5 days. The reaction mixture was diluted with methylene chloride. The result was washed with a potassium carbonate aqueous solution and water in this order, and then dried over magnesium sulfate. After filtering, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→methylene chloride:methanol=9:1) to afford the title compound as a yellow powder (0.46 g).

Workup

  1. washThe result was washed with a potassium carbonate aqueous solution and water in this order
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtering
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (methylene chloride:methanol=1:0→methylene chloride:methanol=9:1)

Sources & evidence

ORD record
ord-42d739a7535147788e56975c9645da1d
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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