Methylamine → HCID 178482074, compound

HRID 45849Notes

Reaction equation

HRID 45849 reaction equation
[CH2:1]([N:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:9]1[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](F)[CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:10]=1[F:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][NH2:37]>CS(C)=O.O>[CH2:29]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[C:10]([F:28])=[C:11]([C:16]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:37][CH3:36])[CH:22]=3)=[CH:19][NH:18][N:17]=2)[C:12]([F:15])=[CH:13][CH:14]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 178505449HCID 178505449, compound

Product 1

HCID 178482074HCID 178482074, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of dibenzyl-{2,4-difluoro-3-[4-(2-fluoro-pyridin-4-yl)-1H-pyrazol-3-yl]-phenyl}-amine (400 mg, 0.849 mmol) in DMSO (4.24 mL), a 40% methyl amine solution in water (3.5 mL) was added. The mixture was irradiated in the microwave oven at 120° C. for one hour and then poured into water and extracted with ethyl acetate. The organic layer was washed three times with saturated aqueous NaHCO3 and once with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduce pressure and the crude product was used in the following step without further purification.

Workup

  1. customThe mixture was irradiated in the microwave oven at 120° C. for one hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed three times with saturated aqueous NaHCO3
  4. dry with materialonce with brine, dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customthe crude product was used in the following step without further purification

Sources & evidence

ORD record
ord-23616c5d162645c99aec266358e96c96
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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