1-Hydroxybenzotriazole → HCID 86709406, compound

HRID 2172272Notes

Reaction equation

HRID 2172272 reaction equation
ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[N+:23]([C:26]1[N:27]=[C:28]2[N:33]([CH:34]=1)[CH2:32][CH2:31][C@H:30]([CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([N:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)=[CH:39][CH:38]=1)[O:29]2)([O-:25])=[O:24].[F:49][C:50]([F:62])([F:61])[C:51]1[CH:52]=[C:53]([OH:60])[C:54](=[CH:58][CH:59]=1)[C:55](O)=[O:56]>O.CN(C=O)C>[OH:60][C:53]1[CH:52]=[C:51]([C:50]([F:49])([F:61])[F:62])[CH:59]=[CH:58][C:54]=1[C:55]([N:46]1[CH2:47][CH2:48][N:43]([C:40]2[CH:41]=[CH:42][C:37]([O:36][CH2:35][C@@H:30]3[O:29][C:28]4=[N:27][C:26]([N+:23]([O-:25])=[O:24])=[CH:34][N:33]4[CH2:32][CH2:31]3)=[CH:38][CH:39]=2)[CH2:44][CH2:45]1)=[O:56]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 1645782-Hydroxy-4-(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70874384HCID 70874384, compound

Product 1

HCID 86709406HCID 86709406, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (0.19 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.24 g) were added to a DMF solution (5 ml) of (R)-2-nitro-7-(4-piperazin-1-ylphenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.40 g) and 4-(trifluoromethyl)salicylic acid (0.25 g), and the mixture was stirred at room temperature for 11 hours. Water was added to the reaction mixture. After stirring the mixture for a while, the precipitate was collected by filtration. The resulting crude product was purified by silica gel column chromatography (methylene chloride:methanol=90:10) and recrystallized from ethanol-acetone to afford the title compound as a white powder (0.42 g).

Workup

  1. stirringAfter stirring the mixture for a while
  2. filtrationthe precipitate was collected by filtration
  3. customThe resulting crude product was purified by silica gel column chromatography (methylene chloride:methanol=90:10)
  4. customrecrystallized from ethanol-acetone

Sources & evidence

ORD record
ord-7df0c28f5d7a4d64806c4fa21c60c98d
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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