Tetrahydrofuran → HCID 178496031, compound

HRID 571430Notes

Reaction equation

HRID 571430 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[N:8][C:9](Cl)=[CH:10][C:5]=2[NH:4][N:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH:16][C:17]([NH2:19])=[O:18].CC([O-])(C)C.[K+].C1COCC1>>[Cl:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH:19][C:17]([NH:16][CH2:15][CH2:14][O:13][CH3:12])=[O:18])=[CH:10][C:5]=2[NH:4][N:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 186068(2-Methoxyethyl)ureaHCID 23665647Potassium tert-butoxideHCID 178477830HCID 178477830, compound

Product 1

HCID 178496031HCID 178496031, compoundYield 25.6%

Conditions

Temperature
60 °C

Procedure

A mixture of 3,6-dichloro-1H-pyrazolo[4,3-c]pyridine (583.6 mg, 3.10 mmol), 1-(2-methoxyethyl)urea (550 mg, 4.66 mmol), chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′-4′-6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II) (248 mg, 0.310 mmol) and 1.78 M KOtBu in THF (5231 μl, 9.31 mmol) was degassed and then THF (0.5 mL) was added. The reaction mixture was heated to 60° C. overnight. The reaction was diluted with ethyl acetate and washed with water. The combined organics were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by MPLC (0-30% MeOH-DCM) gave 1-(3-chloro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(2-methoxyethyl)urea (214 mg, 0.794 mmol, 25.6% yield). MS ESI calc'd. for C10H13ClN5O2 [M+H]+ 270, found 270.

Workup

  1. customwas degassed
  2. additionTHF (0.5 mL) was added
  3. additionThe reaction was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by MPLC (0-30% MeOH-DCM)

Sources & evidence

ORD record
ord-82637d4a70f34829bfe47beb7ee23aca
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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