1,2-Dichloroethane → HCID 178522595, compound

HRID 1821344Notes

Reaction equation

HRID 1821344 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:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14](O)=[O:15])=[N:2]1.CN1CCOCC1.[NH2:28][C:29]1[N:33]=[CH:32][NH:31][N:30]=1.C(Cl)CCl.O.ON1C2C=CC=CC=2N=N1>C1COCC1.C(OCC)(=O)C.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:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([NH:28][C:29]2[N:33]=[CH:32][NH:31][N:30]=2)=[O:15])=[N:2]1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 27960291-Hydroxybenzotriazole hydrateHCID 57586985(E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acidHCID 178418311HCID 178418311, compound

Product 1

HCID 178522595HCID 178522595, compoundYield 46.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (E)-2-[2-(1H-indazol-3-yl)vinyl]benzoic acid (30 mg, 0.11 mmol) obtained in Step 1 of Example 47 in THF (0.50 mL) was sequentially added with 4-methylmorpholine (25 μL, 0.23 mmol), 3-amino-1,2,4-triazole (14 mg, 0.17 mmol), EDC (31 mg, 0.16 mmol) and 1-hydroxybenzotriazole monohydrate (20 mg, 0.15 mmol) followed by stirring at room temperature for 2.0 hours. The reaction mixture was added organic layer and aqueous layer and the organic layer was with water and ethyl acetate to separate the mixture into concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10) to obtain Compound 139 (17 mg, 45%).

Workup

  1. additionThe reaction mixture was added organic layer and aqueous layer
  2. customto separate the mixture
  3. concentrationinto concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 90/10)

Sources & evidence

ORD record
ord-68cffc05b64c425c9733ef06bd7449d1
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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