Diisopropylethylamine → 6-Chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-3-nitropyridin-2-amine

HRID 450360Notes

Reaction equation

HRID 450360 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH:12]1([C:15]2[NH:19][N:18]=[C:17]([NH2:20])[CH:16]=2)[CH2:14][CH2:13]1.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:11][C:4]1[N:3]=[C:2]([NH:20][C:17]2[CH:16]=[C:15]([CH:12]3[CH2:14][CH2:13]3)[NH:19][N:18]=2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 27580143-cyclopropyl-1H-pyrazol-5-amine

Product 1

HCID 589359036-Chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)-3-nitropyridin-2-amineYield 69%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,6-dichloro-3-nitropyridine (5 g) and 5-cyclopropyl-1H-pyrazol-3-amine (5 g) in acetonitrile (40 mL) with diisopropylethylamine (6 mL) was stirred at room temperature for 24 hours, The resulting mixture was concentrated, and the resulting residue was separated by silica gel column (Hexane/Ethyl acetate) to afford 5 g desired product. MS (electrospray): 280 (M+1) for C11H10ClN5O2. 1H NMR (300 MHz, CD3OD) δ ppm 8.5 (d, 1H) 6.9 (d, 1H) 6.5 (s, 1H) 1.9 (m, 1H) 1.0 (m, 2H) 0.70 (m, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe resulting residue was separated by silica gel column (Hexane/Ethyl acetate)

Sources & evidence

ORD record
ord-b5ab107d24b34a7a80ff539c0561fa11
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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