Diisopropylethylamine → HCID 23591843, compound

HRID 1611718Notes

Reaction equation

HRID 1611718 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])[CH:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:36]1[N:41]=[C:40]([NH2:42])[C:39]([N+:43]([O-:45])=[O:44])=[CH:38][CH:37]=1>C(#N)C>[Cl:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[C:7]1[C:8]([CH2:11][N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:9][CH:10]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:36]2[N:41]=[C:40]([NH2:42])[C:39]([N+:43]([O-:45])=[O:44])=[CH:38][CH:37]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 22254151HCID 22254151, compound

Product 1

HCID 23591843HCID 23591843, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

The amine hydrochloride salt 10 (35 mg) in acetonitrile (2 ml) is treated with N,N-diisopropylethylamine (54 eq) and 6-chloro-3-nitro-2-pyridylamine 11 (1.2 eq) and stirred at 90° C. for 2 h. The mixture is concentrated under reduced pressure and dried under vacuum. The crude product is purified by chromatography starting with 3% MeOH in methylene chloride and finishing with, 5% MeOH in methylene chloride to provide 12 as yellow solid (50–70%). The material is acidified with 2 equivalents of HCl and lyophilized to a dry powder.

Workup

  1. concentrationThe mixture is concentrated under reduced pressure
  2. customdried under vacuum
  3. customThe crude product is purified by chromatography

Sources & evidence

ORD record
ord-35aff104face48f6b4749b8161acae0c
Source dataset
uspto-grants-2006_01
Patent number
US06989382B2

Reaction notes

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