Ethanol → HCID 13565859, compound

HRID 978206Notes

Reaction equation

HRID 978206 reaction equation
[C:1]([N:4]([CH:23]1[CH2:25][CH2:24]1)[C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:8]([NH2:22])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(O)C.[F:29][B-:30]([F:33])([F:32])[F:31].[H+].[N:35]([O-])=O.[Na+]>O.CCOCC>[F:29][B-:30]([F:33])([F:32])[F:31].[CH2:20]([O:19][C:17]([N:14]1[CH2:15][CH2:16][N:11]([C:9]2[C:8]([N+:22]#[N:35])=[CH:7][CH:6]=[C:5]([N:4]([C:1](=[O:3])[CH3:2])[CH:23]3[CH2:24][CH2:25]3)[N:10]=2)[CH2:12][CH2:13]1)=[O:18])[CH3:21]

Participants

7

Reactant 4

HCID 702EthanolHCID 28118Tetrafluoroboric acidHCID 13565853HCID 13565853, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13565859HCID 13565859, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 20.8 g (60 mmole) of 4-[6-(acetylcyclopropylamino)-3-amino-2-pyridinyl]-1-piperazinecarboxylic acid, ethyl ester, 44 ml of ethanol and 27 ml of 48% tetrafluoroboric acid was cooled to 0° C. and treated dropwise with a solution of 4.56 g (66 mmol) of sodium nitrite in 8 ml of water under a nitrogen atmosphere keeping the temperature 0°-5° C. After the addition was complete, the reaction was stirred at 0°-5° C. for one hour and treated with 150 ml of anhydrous ether keeping the temperature below 10° C. The solid was removed by filtration, the precipitate was washed with ethanol/ether (1:1), ether and dried in vacuo to give 24.5 g of the title compound, mp 100°-105° C. (dec.).

Workup

  1. customthe temperature 0°-5° C
  2. additionAfter the addition
  3. customThe solid was removed by filtration
  4. washthe precipitate was washed with ethanol/ether (1:1), ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bc9a6be9cd11450c81cfd713c01adf57
Source dataset
uspto-grants-1987_05
Patent number
US04663457

Reaction notes

Loading…