Nitrogen → HCID 90019740, compound

HRID 2175059Notes

Reaction equation

HRID 2175059 reaction equation
N#N.Cl[C:4]1[N:9]=[C:8]([NH:10][C@H:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=3)[CH2:13][CH2:12]2)[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=1.[CH3:24][C:25]1[NH:29][N:28]=[C:27]([NH2:30])[CH:26]=1.C(N(C(C)C)CC)(C)C>CO.O.CS(C)=O>[F:20][C:17]1[CH:18]=[C:19]2[C:14]([CH2:13][CH2:12][C@H:11]2[NH:10][C:8]2[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][CH:5]=[C:4]([NH:30][C:27]3[CH:26]=[C:25]([CH3:24])[NH:29][N:28]=3)[N:9]=2)=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 947NitrogenHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 90019210HCID 90019210, compound

Product 1

HCID 90019740HCID 90019740, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Equip a 3 neck flask (22 L) with a thermocouple, condenser, overhead stirrer, N2 inlet, and heating mantle. To the flask, charge 6-chloro-N-[(1R)-6-fluoro-2,3-dihydro-1H-inden-1-yl]-3-nitropyridin-2-amine (600 g, 1.95 mol), 5-methyl-1H-pyrazol-3-amine (208.31 g, 2.14 mol), dimethylsulfoxide (6.0 L), and diisopropylethylamine (680.11 mL, 3.90 moles). Stir the solution at 70° C. for 20 hours. Cool the mixture to ambient temperature and dilute it with MeOH (6.0 L). Add de-ionized water (2.1 L) to the solution over one hour to give in an orange suspension. Stir the suspension for one hour, and then filter through polypropylene. Wash the filter cake with de-ionized water (12 L), transfer the solid to a tared dish and vacuum-dry (50° C.) to constant weight to provide the title compound (647 g, 90%). MS (m/z): 369 (M+1).

Workup

  1. temperatureheating mantle
  2. temperatureCool the mixture to ambient temperature
  3. customto give in an orange suspension
  4. stirringStir the suspension for one hour
  5. filtrationfilter through polypropylene
  6. washWash the filter cake with de-ionized water (12 L)
  7. customvacuum-dry (50° C.) to constant weight

Sources & evidence

ORD record
ord-cc7e99e91f3e4db893a4a6336e9fae8b
Source dataset
uspto-grants-2015_06
Patent number
US09062050B2

Reaction notes

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