2-Nitrobenzoic acid → HCID 87549939, compound

HRID 1895976Notes

Reaction equation

HRID 1895976 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].ON1C2C=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]#[C:42][CH:43]=[C:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[N:36]=1>C(Cl)Cl.CN(C=O)C>[CH3:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37]([C:41]#[C:42][CH:43]=[C:44]2[CH2:45][CH2:46][N:47]([C:6](=[O:8])[C:5]3[CH:9]=[CH:10][CH:11]=[CH:12][C:4]=3[N+:1]([O-:3])=[O:2])[CH2:48][CH2:49]2)[N:36]=1

Participants

7

Reactant 4

HCID 110872-Nitrobenzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

Product 1

HCID 87549939HCID 87549939, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution 2-nitrobenzoic acid (42.6 mg, 0.25 mmol) in CH2Cl2 (2 mL) and DMF (0.5 mL) stirred at 0-5° C., was added 1-hydroxybenzotriazole (50 mg, 0.322 mmol) and, after 30′, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (62 mg, 0.323 mmol). Afterwards, the Compound of Example 3 (53 mg, 0.25 mmol) was added. The reaction mixture was stirred at r.t. for 2 h and kept overnight at the same temperature. After dilution with water and 1 N NaOH, the organic layer was separated and washed with water, dried over Na2SO4 and evaporated to dryness in vacuo. Purification by flash chromatography (CHCl3-1.4 N MeOH/NH3 100:0.1) yielded the title compound (82 mg).

Workup

  1. waitkept overnight at the same temperature
  2. customAfter dilution with water and 1 N NaOH, the organic layer was separated
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customPurification by flash chromatography (CHCl3-1.4 N MeOH/NH3 100:0.1)

Sources & evidence

ORD record
ord-1c26939fec704b44af6e1d766a73e1eb
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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