1H-indazol-3-amine → HCID 66623528, compound

HRID 2063582Notes

Reaction equation

HRID 2063582 reaction equation
C(N(CC)C(C)C)(C)C.[NH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:13][N:12]=1.Cl[C:21]1[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:25][N:24]=[C:23]([S:32][CH3:33])[N:22]=1>O1CCCC1>[NH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([NH:10][C:25]2[C:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21][N:22]=[C:23]([S:32][CH3:33])[N:24]=2)=[N:12]1

Participants

5

Reactant 3

HCID 133991H-indazol-3-amineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 66623528HCID 66623528, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N-diisopropylethylamine (19.4 g) and 3-aminoindazole (6.66 g) were added to a tetrahydrofuran (0.2 L) solution of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (12.22 g), and stirred with heating under reflux for 15 hours. After cooled to room temperature, the reaction solution was evaporated under reduced pressure, water (50 mL) was added to the residue and the precipitated solid was collected through filtration, washed with distilled water and ethyl acetate in that order, and dried to give the title compound as a white solid (14.3 g).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hours
  3. customthe reaction solution was evaporated under reduced pressure, water (50 mL)
  4. additionwas added to the residue
  5. filtrationthe precipitated solid was collected through filtration
  6. washwashed with distilled water and ethyl acetate in that order
  7. customdried

Sources & evidence

ORD record
ord-1c766b6931d64b2aa553eed305147bef
Source dataset
uspto-grants-2012_10
Patent number
US08288396B2

Reaction notes

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