2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 57756249, compound

HRID 593956

Reaction equation

HRID 593956 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[NH2:30][C:31]1[CH:51]=[CH:50][C:34]([O:35][C:36]2[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[C:44]([NH:48][CH3:49])[CH:43]=3)=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:33][CH:32]=1.Cl[C:53]1[C:58]2[CH2:59][CH2:60][CH2:61][C:57]=2[C:56]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[N:55][N:54]=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:49][NH:48][C:44]1[CH:43]=[C:42]([C:41]2[C:36]([O:35][C:34]3[CH:50]=[CH:51][C:31]([NH:30][C:53]4[N:54]=[N:55][C:56]([C:62]5[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=5)=[C:57]5[CH2:61][CH2:60][CH2:59][C:58]=45)=[CH:32][CH:33]=3)=[N:37][CH:38]=[CH:39][CH:40]=2)[CH:47]=[CH:46][N:45]=1

Participants

6

Reactant 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 667351614-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amineHCID 866141641-Chloro-6,7-dihydro-4-phenyl-5H-cyclopenta[d]pyridazine

Product 1

HCID 57756249HCID 57756249, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A resealable reaction tube was charged with tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.021 g, 0.051 mmol), 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amine (0.075 g, 0.257 mmol), 1-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazine (0.059 g, 0.257 mmol), and sodium tert-butoxide (0.035 g, 0.359 mmol). This mixture was purged with nitrogen for several minutes, followed by addition of 0.780 mL of toluene. The vial was capped and heated at 100° C. for 1.5 h. Upon cooling, ethyl acetate was added and a precipitate formed. After filtration and washing with EtOAc, the crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column), to provide N-(4-(3-(2-(methylamino)pyridin-4-yl)pyridin-2-yloxy)phenyl)-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazin-1-amine as a tan solid. MS m/z=487 [M+H]+. Calc'd for C30H26N6O: 486.57.

Workup

  1. customThis mixture was purged with nitrogen for several minutes
  2. additionfollowed by addition of 0.780 mL of toluene
  3. customThe vial was capped
  4. temperatureUpon cooling
  5. additionethyl acetate was added
  6. customa precipitate formed
  7. filtrationAfter filtration
  8. washwashing with EtOAc
  9. customthe crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column)

Sources & evidence

ORD record
ord-0a1e5b278abe4ef89c9597d01ecd7bac
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Linked notes

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