1,2-Dichloroethane → HCID 69001045, compound

HRID 1821384Notes

Reaction equation

HRID 1821384 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([C:21]2[N:29]=[CH:28][CH:27]=[CH:26][C:22]=2[C:23]([OH:25])=O)=[O:20])=[N:2]1.N1C2C(=CC=CC=2)C(/C=C/C2C=CC=CC=2NC(C2C(C(O)=O)=NC=CC=2)=O)=N1.O.ON1C2C=CC=CC=2N=N1.C(Cl)CCl>C1COCC1.O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N:18]2[C:23](=[O:25])[C:22]3[C:21](=[N:29][CH:28]=[CH:27][CH:26]=3)[C:19]2=[O:20])=[N:2]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 68999942HCID 68999942, compoundHCID 69002709HCID 69002709, compound

Product 1

HCID 69001045HCID 69001045, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-2-{2-[2-(1H-indazol-3-yl)vinyl]phenylcarbamoyl}nicotinic acid or (E)-3-{2-[2-(1H-indazol-3-yl)vinyl]phenylcarbamoyl}pyridine-2-carboxylic acid (20 mg, 0.052 mmol) obtained in Step 1 in THF (1.0 mL), 1-hydroxybenzotriazole monohydrate (1.6 mg, 0.010 mmol) and EDC (15 mg, 0.078 mmol) were added, followed by heating under reflux for 30 minutes. The reaction mixture was added with water, extracted with ethyl acetate and the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10), crystallized from DMF/water (1/1) to obtain Compound 205 (7.2 mg, 38%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 30 minutes
  3. extractionextracted with ethyl acetate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=90/10)
  6. customcrystallized from DMF/water (1/1)

Sources & evidence

ORD record
ord-abcf9d959ee247a3af0a3aa24cd2a242
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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