Diisopropylethylamine → HCID 178428236, compound

HRID 2175054Notes

Reaction equation

HRID 2175054 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([F:18])[CH:16]=3)[CH2:11][CH2:10]2)[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=1.[NH2:22][C:23]1[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[F:18][C:15]1[CH:16]=[C:17]2[C:12]([CH2:11][CH2:10][CH:9]2[NH:8][C:6]2[C:5]([N+:19]([O-:21])=[O:20])=[CH:4][CH:3]=[C:2]([NH:22][C:23]3[NH:24][N:25]=[C:26]([CH3:28])[CH:27]=3)[N:7]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 90027018HCID 90027018, compound

Product 1

HCID 178428236HCID 178428236, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Combine 6-chloro-N-(6-fluoro-2,3-dihydro-1H-inden-1-yl)-3-nitropyridin-2-amine (9.00 g, 29.34 mmol) and 3-amino-5-methylpyrazole (4.56 g, 46.95 mmol) in dimethylsulfoxide (60 mL). Add N,N-diisopropylethylamine (8.18 mL, 46.95 mmol) and heat the reaction under nitrogen at 120° C. for 90 minutes. Pour the reaction into ice water (200 mL) and stir 20 minutes, then filter. Suspend the solid obtained in a mixture of dichloromethane and methanol and stir at 40° C. for 20 minutes. Filter the mixture to give the title compound as a yellow solid (6.03 g, 56%). MS (ES) m/z=369 [M+1].

Workup

  1. customthe reaction under nitrogen at 120° C. for 90 minutes
  2. additionPour
  3. filtrationfilter
  4. customobtained in a mixture of dichloromethane and methanol
  5. stirringstir at 40° C. for 20 minutes
  6. filtrationFilter the mixture

Sources & evidence

ORD record
ord-f3348e88bfa6454896c33c1bfa9db1ae
Source dataset
uspto-grants-2015_06
Patent number
US09062050B2

Reaction notes

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