1-Hydroxybenzotriazole → HCID 117987919, compound

HRID 2205968Notes

Reaction equation

HRID 2205968 reaction equation
[I:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1.Cl.[CH:14]1([NH:20][NH2:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O.C(N(CC)CC)C>[CH:14]1([NH:20][NH:21][C:8](=[O:10])[C:7]2[C:2]([I:1])=[CH:3][CH:4]=[N:5][C:6]=2[O:11][CH3:12])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 207836Cyclohexylhydrazine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

Product 1

HCID 117987919HCID 117987919, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 4-iodo-2-methoxynicotinic acid (558 mg), cyclohexyl hydrazine hydrochloride (362 mg), EDCI hydrochloride (575 mg), HOBt (405 mg) and triethylamine (304 mg) in DMF (10 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (515 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1ff4876ebac64acb92072521aac289aa
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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