Diisopropylethylamine → HCID 117667243, compound

HRID 1526250Notes

Reaction equation

HRID 1526250 reaction equation
Cl[C:2]1[C:3]([C:13]([NH2:15])=[O:14])=[N:4][C:5]([C:9]([OH:12])([CH3:11])[CH3:10])=[C:6]([Cl:8])[N:7]=1.[NH2:16][C:17]1[CH:18]=[N:19][N:20]([CH2:22][CH2:23][OH:24])[CH:21]=1.C(N(C(C)C)CC)(C)C.C(=O)([O-])O.[Na+]>O1CCOCC1>[Cl:8][C:6]1[N:7]=[C:2]([NH:16][C:17]2[CH:18]=[N:19][N:20]([CH2:22][CH2:23][OH:24])[CH:21]=2)[C:3]([C:13]([NH2:15])=[O:14])=[N:4][C:5]=1[C:9]([OH:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanolHCID 86662050HCID 86662050, compound

Product 1

HCID 117667243HCID 117667243, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3,5-dichloro-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (2.0 g), 2-(4-amino-1H-pyrazol-1-yl)ethan-1-ol (1.12 g), diisopropylethylamine (2.79 mL), and dioxane (20 mL) was heated and refluxed for 2 hours. The reactant was cooled, and then a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with a mixture of chloroform:methanol (10:1). The organic phase was dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10) to obtain 5-chloro-3-{[1-(2-hydroxyethyl)-1H-pyrazol-4-yl]amino}-6-(2-hydroxypropan-2-yl)pyrazine-2-carboxamide (1.69 g) as a yellow solid.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours
  3. temperatureThe reactant was cooled
  4. extractionfollowed by extraction with a mixture of chloroform:methanol (10:1)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol=99:1-90:10)

Sources & evidence

ORD record
ord-bae13a200cfd49d8831e023bd6ae69e5
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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