Water → HCID 178463993, compound

HRID 336851Notes

Reaction equation

HRID 336851 reaction equation
[C:1]([C:3]1[C:4]([CH3:25])=[C:5]2[C:20]([C:21]([NH:23][NH2:24])=[O:22])=[N:19][NH:18][C:6]2=[N:7][C:8]=1[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=1[F:17])#[N:2].[CH2:26]([N:28]([CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][N:32]=[C:33]=S)[CH3:27].Cl.C(N=C=NCCCN(C)C)C.O>CC(N(C)C)=O>[CH2:26]([N:28]([CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][NH:32][C:33]1[O:22][C:21]([C:20]2[C:5]3[C:6](=[N:7][C:8]([C:9]4[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=4[F:17])=[C:3]([C:1]#[N:2])[C:4]=3[CH3:25])[NH:18][N:19]=2)=[N:23][N:24]=1)[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27582403-(Diethylamino)propyl isothiocyanateHCID 178488915HCID 178488915, compound

Product 1

HCID 178463993HCID 178463993, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
65 °C

Procedure

To 200 mg (0.59 mmol) of 5-cyano-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-3-carbohydrazide diluted in 8 ml of dimethylacetamide, are added 101 mg of N,N-diethyl-3-isothiocyanatopropane-1-amine. The reaction mixture is stirred at 65° C. until complete disappearance of the starting product. 224 mg (1.17 mmol) of N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride are added and the solution is stirred at 70° C. for 2 h. 20 ml of water are added and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, and concentrated. The solid is triturated in a diethyl ether/methanol mixture (10:1) to yield 170 mg of 3-(5-(3-(diethylamino)propylamino)-1,3,4-oxadiazol-2-yl)-6-(2-fluoro-4-methoxyphenyl)-4-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile in the form of a pink solid.

Workup

  1. stirringthe solution is stirred at 70° C. for 2 h
  2. extractionthe product is extracted several times with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe solid is triturated in a diethyl ether/methanol mixture (10:1)

Sources & evidence

ORD record
ord-2624957d196f47918bc4605cbac2d512
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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