3-Nitrobenzoic acid → n-(2-{[4-(4-Cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)(3-nitrophenyl)carboxamide

HRID 2297126Notes

Reaction equation

HRID 2297126 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][CH:12]=2)[C:8]([C:19]2[NH:20][CH:21]=[CH:22][N:23]=2)=[CH:7][N:6]=1.[N+:24]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](O)=[O:31])([O-:26])=[O:25].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CC(N(C)C)=O.C(OCC)(=O)C>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]2[C:8]([C:19]3[NH:23][CH:22]=[CH:21][N:20]=3)=[CH:7][N:6]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][C:30]([C:29]3[CH:33]=[CH:34][CH:35]=[C:27]([N+:24]([O-:26])=[O:25])[CH:28]=3)=[O:31])[N:10]=2)=[CH:12][CH:13]=1)#[N:18]

Participants

8

Reactant 4

HCID 84973-Nitrobenzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 572319134-{2-[(2-Aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile

Product 1

HCID 57324312n-(2-{[4-(4-Cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)(3-nitrophenyl)carboxamideYield 71.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 4-{2-[(2-aminoethyl)amino]-5-imidazolylpyrimidin-4-yl}benzenecarbonitrile (30 mg, 0.098 mmol), 3-nitrobenzoic acid (17 mg, 0.1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (19 mg, 0.1 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (14 mg, 0.1 mmol), and 4-dimethylaminopyridine (DMAP) (12 mg, 0.1 mmol) in DMA (500 uL) were stirred at room temperature. After 12 hours, the reaction was diluted with ethyl acetate (10 ml) and extracted with sat. aq. NaHCO3 (2×5 ml), water (3×5 ml), brine (5 ml), dried with Na2SO4, filtered, and concentrated. The resulting product, N-(2-{[4-(4-cyanophenyl)-5-imidazolylpyrimidin-2-yl]amino}ethyl)(3-nitrophenyl)carboxamide weighing 32 mg (70% yield) was approximately 95% pure by LCMS and HPLC.

Workup

  1. extractionextracted with sat. aq. NaHCO3 (2×5 ml), water (3×5 ml), brine (5 ml)
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fecb44207f374cd6a2b031de628cc873
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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