Triethylamine → HCID 86620617, compound

HRID 75920

Reaction equation

HRID 75920 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[CH:11]1([C:14]2[NH:18][N:17]=[C:16]([NH2:19])[CH:15]=2)[CH2:13][CH2:12]1.C(N(CC)CC)C>CN1C(=O)CCC1>[Cl:8][C:7]1[C:2]([NH:19][C:16]2[CH:15]=[C:14]([CH:11]3[CH2:13][CH2:12]3)[NH:18][N:17]=2)=[N:3][C:4]([Cl:10])=[C:5]([Cl:9])[CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 169902,3,5,6-TetrachloropyridineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 86620617HCID 86620617, compoundYield 12.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2,3,5,6-tetrachloropyridine (0.20 g, 0.9 mmol), 5-cyclopropyl-1H-pyrazol-3-amine (0.20 g, 1.8 mmol), and triethylamine (0.10 g, 1.4 mmol) in NMP (2 ml) was heated in a microwave at 200° C. for 30 min. The reaction was cooled to 25° C., quenched with water (10 ml), and extracted with MTBE (4×30 ml). The combined organic fractions were then dried, filtered, and concentrated. The resulting solid was purified by column chromatography (DCM-MeOH=50:1) to give the title compound (0.035 g, 12%). MS: Calcd.: 303. Found: [M+H]+ 303.

Workup

  1. customquenched with water (10 ml)
  2. extractionextracted with MTBE (4×30 ml)
  3. customThe combined organic fractions were then dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting solid was purified by column chromatography (DCM-MeOH=50:1)

Sources & evidence

ORD record
ord-3643896c5c1445239f78c61f23e2ad2a
Source dataset
uspto-grants-2014_09
Patent number
US08835465B2

Linked notes

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