Diisopropylethylamine → HCID 23591844, compound

HRID 1611706Notes

Reaction equation

HRID 1611706 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13](F)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17].[NH2:19][C:20]1[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=[C:22]([NH:29][CH2:30][CH2:31][NH2:32])[N:21]=1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[CH:11][CH:12]=[C:13]([NH:32][CH2:31][CH2:30][NH:29][C:22]2[N:21]=[C:20]([NH2:19])[C:25]([N+:26]([O-:28])=[O:27])=[CH:24][CH:23]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 221423802,6-Diamino-N2-(2-aminoethyl)-5-nitropyridineHCID 22254166HCID 22254166, compound

Product 1

HCID 23591844HCID 23591844, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 2-(2,4-dichlorophenyl)-4-fluoro-1-nitrobenzene (20 mgs, 0.06 mmol) in N,N-dimethylformamide was added 2-amino-3-nitro-6-(2-aminoethylamino)pyridine (14 mgs, 0.07 mmol) and N,N-diisopropylethyl amine (16 μl, 0.07 mmol) and heated to 80° C. over-night. The mixture was partitioned between ethyl acetate and water and the organic layer was dried (MgSO4) and concentrated. Purification on silica gel with 5% methanol in dichloromethane as eluent yielded 7 mgs of N˜6˜-{2-[(2′,4′-dichloro-6-nitro-1,1′-biphenyl-3-yl)amino] ethyl}-3-nitropyridine-2,6-diamine.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customPurification on silica gel with 5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-f5b48532d3bc457586dc2bc0f4260930
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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