1,2-Dichloroethane → HCID 67337609, compound

HRID 1184534Notes

Reaction equation

HRID 1184534 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)[CH:8]=[CH:9][C:10]=1[F:11])(=[O:3])[CH3:2].[CH2:17]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[NH2:33])[CH:26]=[N:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH2:17]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][C:31]=2[NH:33][C:14](=[O:16])/[CH:13]=[CH:12]/[C:7]2[CH:8]=[CH:9][C:10]([F:11])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[CH:6]=2)[CH:26]=[N:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 58387451HCID 58387451, compoundHCID 67337594HCID 67337594, compound

Product 1

HCID 67337609HCID 67337609, compoundYield 8.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (E)-3-(3-acetoxy-4-fluoro-phenyl)-acrylic acid (119 mg, 0.53 mmol), 1-benzyl-1H-indazol-7-ylamine (118 mg, 0.53 mmol), EDC (123 mg, 0.64 mmol) and HOBT (36 mg, 0.27 mmol) in DMF (3 ml) was stirred at RT for 48 hrs. The mixture was then diluted with water and extracted with AcOEt. The organic layer was dried over sodium sulphate and evaporated to dryness. The crude was purified by column chromatography (petroleum ether:AcOEt from 9:1 to 1:1) to give the title (E)-N-(1-benzyl-1H-indazol-7-yl)-3-(4-fluoro-3-acetoxy-phenyl)-acrylamide (19 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. customevaporated to dryness
  4. customThe crude was purified by column chromatography (petroleum ether:AcOEt from 9:1 to 1:1)

Sources & evidence

ORD record
ord-c0ca4dcadd294f53a230ffcacf658caf
Source dataset
uspto-grants-2014_03
Patent number
US08669261B2

Reaction notes

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