Acetaldehyde → HCID 86709405, compound

HRID 2172269Notes

Reaction equation

HRID 2172269 reaction equation
[CH:1](=O)[CH3:2].[N+:4]([C:7]1[N:8]=[C:9]2[N:14]([CH:15]=1)[CH2:13][CH2:12][C@H:11]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][CH:27]([NH:30][C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)[CH2:26][CH2:25]3)=[CH:20][CH:19]=1)[O:10]2)([O-:6])=[O:5].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH2:1]([N:30]([CH:27]1[CH2:28][CH2:29][N:24]([C:21]2[CH:20]=[CH:19][C:18]([O:17][CH2:16][C@@H:11]3[O:10][C:9]4=[N:8][C:7]([N+:4]([O-:6])=[O:5])=[CH:15][N:14]4[CH2:13][CH2:12]3)=[CH:23][CH:22]=2)[CH2:25][CH2:26]1)[C:31]1[CH:32]=[CH:33][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:35][CH:36]=1)[CH3:2]

Participants

7

Reactant 5

HCID 177AcetaldehydeHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 70874872HCID 70874872, compound

Product 1

HCID 86709405HCID 86709405, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetaldehyde (2.2 ml) was added to an acetic acid solution (11 ml) of N-{1-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-yl}-N-(4-trifluoromethylphenyl)amine (2.2 g). Subsequently, sodium triacetoxyborohydride (2.52 g) was added thereto, and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice water, and neutralized with a 5 N sodium hydroxide aqueous solution and a saturated sodium hydrogen carbonate aqueous solution. The resulting precipitate was collected by filtration and dried. The solid thus obtained was purified by silica gel column chromatography (methylene chloride:ethyl acetate=50:50) and recrystallized from acetone-ethyl acetate to afford the title compound as a yellow powder (1.96 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried
  3. customThe solid thus obtained
  4. customwas purified by silica gel column chromatography (methylene chloride:ethyl acetate=50:50)
  5. customrecrystallized from acetone-ethyl acetate

Sources & evidence

ORD record
ord-b52fe7564ec84938a274164b008137ba
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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