Diisopropylethylamine → HCID 22254179, compound

HRID 1611707Notes

Reaction equation

HRID 1611707 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][CH2:20][CH2:21][NH:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[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:19][CH2:20][CH2:21][NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][N:24]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 113694056-[(2-Aminoethyl)amino]pyridine-3-carbonitrileHCID 22254166HCID 22254166, compound

Product 1

HCID 22254179HCID 22254179, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

To 2-(2,4-dichlorophenyl)-4-fluoro-1-nitrobenzene(32 mgs, 0.1 mmol) in acetonitrile was added 2-(2-aminoethylamino)-5-cyanopyridine (19.2 mgs, 0.1 mmol) and N,N diisopropylethylamine (18 μl, 0.1 mmol), and the mixture was heated to 85° 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 the eluent yielded 25 mgs of 6-({2-[(2′,4′-dichloro-6-nitro-1,1′-biphenyl-3-yl)amino]ethyl}amino)nicotinonitrile.

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 the eluent

Sources & evidence

ORD record
ord-d5e81faa6fad430fb78e9fdb64e73ae7
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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