Triethylamine → HCID 86711681, compound

HRID 710657Notes

Reaction equation

HRID 710657 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][C:13]3[N:17]([C:20]4[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=4)[N:18]=[CH:19][C:12]2=3)=[O:10])[CH:7]=1)#[N:2].[NH2:27][OH:28].Cl.CCN(CC)CC>CCO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([N:17]2[C:13]3[CH2:14][CH2:15][CH2:16][N:11]([C:9](=[O:10])[CH2:8][N:6]4[CH:7]=[C:3]([C:1]([NH2:2])=[N:27][OH:28])[CH:4]=[N:5]4)[C:12]=3[CH:19]=[N:18]2)=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 86711680HCID 86711680, compound

Product 1

HCID 86711681HCID 86711681, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-(4-cyanopyrazol-1-yl)-1-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]ethanone (0.175 g, 0.50 mmol), NH2OH—HCl (0.500 g, 7.2 mmol) and NEt3 (1.00 mL, 7.1 mmol) in EtOH (3 mL) was heated at 90° C. for 5 hrs. It was then cooled to rt. The mixture was partitioned between IPA/CHCl3 (1:2, 50 mL) and sat. NaHCO3 (30 mL). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo to obtain 1-[2-[1-(4-fluorophenyl)-6,7-dihydro-5H-pyrazolo[4,3-b]pyridin-4-yl]-2-oxo-ethyl]-N′-hydroxy-pyrazole-4-carboxamidine (0.115 g, 60%).

Workup

  1. temperatureIt was then cooled to rt
  2. customThe mixture was partitioned between IPA/CHCl3 (1:2, 50 mL) and sat. NaHCO3 (30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7a4d4343247c4466b2cdecb5431fae87
Source dataset
uspto-grants-2015_11
Patent number
US09181241B2

Reaction notes

Loading…