Potassium Carbonate → HCID 59598357, compound

HRID 415914Notes

Reaction equation

HRID 415914 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([C:34]2[C:43]3[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=3)[N:37]=[CH:36][CH:35]=2)[OH:33])=[CH:28][CH:27]=1.[CH3:46][C:47]1[N:51]([CH2:52][CH2:53][CH3:54])[N:50]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49](=[O:61])[C:48]=1[C:62](O)=[O:63].C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>CN(C=O)C.ClCCl>[OH:33][CH:32]([C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:44][CH3:45])=[CH:41][CH:42]=2)[N:37]=[CH:36][CH:35]=1)[C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:62]([C:48]2[C:49](=[O:61])[N:50]([C:55]3[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=3)[N:51]([CH2:52][CH2:53][CH3:54])[C:47]=2[CH3:46])=[O:63])=[CH:31][CH:30]=1

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59427360HCID 59427360, compoundHCID 59598360HCID 59598360, compound

Product 1

HCID 59598357HCID 59598357, compoundYield 90.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

In a 10 mL sealed tube under N2, were dissolved HATU (250 mg, 658 μmol), (4-aminophenyl)(7-methoxyquinolin-4-yl)methanol (123 mg, 439 μmol), 5-methyl-3-oxo-2-phenyl-1-propyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (143 mg, 548 mmol) and K2CO3 (182 mg, 1316 mmol) in 2 mL of DMF at rt. After 10 h, the reaction mixture was heated at 60° C. for 3 h and then diluted with dichloromethane, and treated with aqueous NaOH (1N). The aqueous phase was extracted with dichloromethane, and then the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude mixture was purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10) to afford N-(4-(hydroxy(7-methoxyquinolin-4-yl)methyl)phenyl)-5-methyl-3-oxo-2-phenyl-1-propyl-2,3-dihydro-1H-pyrazole-4-carboxamide (208 mg, 90.7% yield) as an off-white solid. MS (ESI pos. ion) m/z: 523 (MH+). Calc'd exact mass for C31H30N4O4: 522. 1H NMR (400 MHz, DMSO-d6) 10.67 (s, 1 H), 8.83 (d, J=4.55 Hz, 1 H), 8.05 (d, J=9.35 Hz, 1 H), 7.53-7.61 (m, 3 H), 7.46-7.52 (m, 3 H), 7.36-7.44 (m, 3 H), 7.31 (d, J=8.59 Hz, 2 H), 7.16 (dd, J=9.16, 2.72 Hz, 1 H), 6.32 (d, J=4.42 Hz, 1 H), 6.15 (d, J=4.29 Hz, 1 H), 3.88 (s, 3 H), 3.79 (t, J=7.20 Hz, 2 H), 2.71 (s, 3 H), 1.33-1.41 (m, 2 H), 0.66 (t, J=7.39 Hz, 3 H).

Workup

  1. customIn a 10 mL sealed tube under N2
  2. extractionThe aqueous phase was extracted with dichloromethane
  3. dry with materialthe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude mixture was purified by MPLC (ISCO, dichloromethane:MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-a76746ee6c3447c49aa21f88e595be26
Source dataset
uspto-grants-2012_01
Patent number
US08088794B2

Reaction notes

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