Ammonia → HCID 178483111, compound

HRID 501435Notes

Reaction equation

HRID 501435 reaction equation
C([N:8]1[C:12]2[C:13]([N:19]([CH3:21])[CH3:20])=[N:14][N:15]([CH3:18])[C:16](=[O:17])[C:11]=2[N:10]=[C:9]1[N:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)C1C=CC=CC=1.N.[Li].[Cl-].[NH4+]>O1CCCC1>[CH3:21][N:19]([CH3:20])[C:13]1[C:12]2[NH:8][C:9]([N:22]3[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:26][CH2:27]3)=[N:10][C:11]=2[C:16](=[O:17])[N:15]([CH3:18])[N:14]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 57472837HCID 57472837, compound

Product 1

HCID 178483111HCID 178483111, compoundYield 7.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 5 ml tetrahydrofuran solution of 0.117 g of t-butyl 4-[1-benzyl-7-dimethylamino-5-methyl-4-oxo-4,5-dihydro-1H-imidazo[4,5-d]pyridazin-2-yl]piperazine-1-carboxylate was added to 15 ml of liquid ammonia, and 0.009 g of lithium was added to the mixture under reflux. 1 ml of a 5% aqueous ammonium chloride solution was added to the solution, and the solvent was evaporated off. The residue was purified by reverse-phase high performance liquid chromatography (using an acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid)) to give 0.007 g of the title compound.

Workup

  1. additionwas added to the mixture
  2. temperatureunder reflux
  3. customthe solvent was evaporated off
  4. customThe residue was purified by reverse-phase high performance liquid chromatography (

Sources & evidence

ORD record
ord-7f6ca62541344758b5a1f749507a118c
Source dataset
uspto-grants-2010_08
Patent number
US07772226B2

Reaction notes

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