Diisopropylamine → HCID 16678494, compound

HRID 1661198Notes

Reaction equation

HRID 1661198 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH:14]=[C:13]([C:15]([OH:17])=O)[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:19][NH:20][CH3:21].C(NC(C)C)(C)C.ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH3:19][N:20]([CH3:21])[C:15]([C:13]1[N:12]=[CH:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:14]=1)=[O:17]

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 10473Dimethylamine, hydrochlorideHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 16128759HCID 16128759, compound

Product 1

HCID 16678494HCID 16678494, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Nitro-phenyl)-1H-imidazole-4-carboxylic acid 2 (0.1 g, 0.4 mmol) was dissolved in DMF (5 mL) and dimethyl amine hydrochloride (33 mg, 0.4 mmol), diisopropyl amine (366 uL, 2.1 mmol), 1-hydroxy-7-azabenzotriazole (HOAt, 68 mg; 0.5 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, hydrochloride (EDC HCl, 96 mg, 0.5 mmol) were added. The mixture was stirred at room temperature for 16 h. The solvent was evaporated and the residue was extracted with hot ethyl acetate. The solvent was evaporated and crystallization from MeOH afforded 30 mg (29%) pure product as white needles. HRMS (ESI+): m/z=260.2518 [M+H]

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with hot ethyl acetate
  3. customThe solvent was evaporated
  4. customcrystallization from MeOH

Sources & evidence

ORD record
ord-b3649b7f8c4e40c2a920d05932ac67db
Source dataset
uspto-grants-2011_10
Patent number
US08030339B2

Reaction notes

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