1-Hydroxybenzotriazole → HCID 117987904, compound

HRID 2206094Notes

Reaction equation

HRID 2206094 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.CCN(C(C)C)C(C)C.Cl.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([CH2:29][NH:30][NH2:31])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[I:1][C:2]1[C:7]([C:8]([NH:31][NH:30][CH2:29][C:28]2[CH:32]=[CH:33][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)=[O:10])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acidHCID 457893744-Methoxybenzylhydrazine hydrochloride

Product 1

HCID 117987904HCID 117987904, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-iodo-2-methoxynicotinic acid (3.00 g) obtained in Step C of Example 6 in DMF (100 mL) were added DIEA (1.88 mL), (4-methoxybenzyl)hydrazine hydrochloride (2.06 g), EDCI hydrochloride (2.03 g) and HOBt (1.45 g) at 0° C., and the mixture 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, filtered, and concentrated under reduced pressure. The residue was washed with ethyl acetate/diisopropyl ether to give the title compound (1.52 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-db59b1850ee7478dbba3c3cd6488fa2b
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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