Nitrogen → HCID 44177142, compound

HRID 341192Notes

Reaction equation

HRID 341192 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[F:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][C:19]3[N:20]([N:22]=[CH:23][C:24]=3B3OC(C)(C)C(C)(C)O3)[CH:21]=2)=[CH:12][CH:11]=1.Cl[C:35]1[CH:40]=[C:39]([NH:41][C:42]([NH:44][CH2:45][CH3:46])=[O:43])[CH:38]=[CH:37][N:36]=1.N#N>O.O1CCOCC1>[CH2:45]([NH:44][C:42]([NH:41][C:39]1[CH:38]=[CH:37][N:36]=[C:35]([C:24]2[CH:23]=[N:22][N:20]3[CH:21]=[C:16]([C:13]4[CH:12]=[CH:11][C:10]([F:9])=[CH:15][CH:14]=4)[CH:17]=[N:18][C:19]=23)[CH:40]=1)=[O:43])[CH3:46]

Participants

7

Reactant 4

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 14625245HCID 14625245, compoundHCID 59277795HCID 59277795, compound

Product 1

HCID 44177142HCID 44177142, compoundYield 18.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of K3PO4 (640 mg, 3 mmol) in H2O (2 ml) was added to a stirred mixture of 6-(4-fluoro-phenyl)-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazolo[1,5-a]pyrimidine (330 mg, 0.97 mmol) and 1-(2-chloro-pyridin-4-yl)-3-ethyl-urea (procedure U4, 420 mg, 2.1 mmol) in dioxane (8 ml) at RT under N2. The mixture was deoxygenated by evacuate/fill N2 (×2), PdCl2dppf (40 mg, 0.05 mmol) was added and the mixture was deoxygenated again (×3). The reaction was stirred and heated at 90° C. for 18 h. After cooling to RT the reaction was partitioned between CH2Cl2/H2O. The aqueous layer was extracted with CH2Cl2 (×1). The combined extracts were dried, then evaporated. The residue was purified by preparative HPLC to give the title compound (68 mg) as a yellow solid.

Workup

  1. customThe mixture was deoxygenated
  2. additionwas added
  3. customthe mixture was deoxygenated again (×3)
  4. temperatureAfter cooling to RT the reaction
  5. customwas partitioned between CH2Cl2/H2O
  6. extractionThe aqueous layer was extracted with CH2Cl2 (×1)
  7. customThe combined extracts were dried
  8. customevaporated
  9. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-954848ff90cb4ec29c1d1565ffa1cb8b
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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