1-Hydroxybenzotriazole → Ammonium Hydroxide

HRID 1858071Notes

Reaction equation

HRID 1858071 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]1[CH2:47][CH2:48][O:49][C:50]1[C:59]2[C:54](=[CH:55][C:56]([Cl:61])=[C:57]([NH2:60])[CH:58]=2)[NH:53][C:52](=[O:62])[C:51]=1[C:63]1[CH:68]=[C:67]([CH3:69])[CH:66]=[C:65]([CH3:70])[CH:64]=1)=[O:40])([CH3:37])([CH3:36])[CH3:35]>C(Cl)Cl.C(N(CC)CC)C>[OH-:10].[NH4+:2].[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][CH2:44][CH2:43][CH:42]1[CH2:47][CH2:48][O:49][C:50]1[C:59]2[C:54](=[CH:55][C:56]([Cl:61])=[C:57]([NH:60][C:9](=[O:11])[CH2:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[CH:58]=2)[NH:53][C:52](=[O:62])[C:51]=1[C:63]1[CH:64]=[C:65]([CH3:70])[CH:66]=[C:67]([CH3:69])[CH:68]=1)=[O:40])([CH3:36])([CH3:35])[CH3:37]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 54025520HCID 54025520, compound

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 54012627HCID 54012627, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a suspension of pyridin-2-yl-acetic acid hydrochloride (60 mg in 0.8 mL methylene chloride) was added 0.051 mL triethylamine and the mixture stirred at room temperature for 10 minutes. At this time, 98 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 69 mg 1-hydroxybenzotriazole, and 60 mg 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (prepared essentially as described in Example 1) were added in order. After 22 hours, the mixture was diluted with methylene chloride and extracted sequentially with water, 10% citric acid and brine. The organic portion was dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (hexane:ethyl acetate, 1:1; then methylene chloride:10% ammonium hydroxide in methanol, 95:5) to give the title compound, 55 mg.

Workup

  1. additionwere added in order
  2. waitAfter 22 hours
  3. extractionextracted sequentially with water, 10% citric acid and brine
  4. dry with materialThe organic portion was dried over sodium sulfate
  5. customthe concentrate purified by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-47e3eecc1a794b12ba547d891149ce32
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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