1,2-Dichloroethane → HCID 69936802, compound

HRID 1623742Notes

Reaction equation

HRID 1623742 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([CH:12]=1)[C:9]([OH:11])=O)[CH3:3].[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([NH2:27])[CH:22]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[CH3:3][CH:2]([C:4]1[CH:5]=[CH:6][C:7]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:8]([CH:12]=1)[C:9]([NH:27][C:23]1[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=1)=[O:11])[CH3:1]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 100093-AminopyridineHCID 757711-HydroxybenzotriazoleHCID 666722601285515-85-6

Product 1

HCID 69936802HCID 69936802, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(1-methylethyl)-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 3; 300 mg, 1.11 mmol), pyridin-3-amine (157 mg, 1.67 mmol), EDC (319 mg, 1.67 mmol) and HOBT (255 mg, 1.665 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was poured into water (20 ml), filtered and the solid was washed with water and dried to yield a white solid. The crude product was purified by silica gel chromatography, eluting with petroleum ether:ethyl acetate (3:1) to yield the title compound as a white solid. 140 mg.

Workup

  1. filtrationfiltered
  2. washthe solid was washed with water
  3. customdried
  4. customto yield a white solid
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with petroleum ether:ethyl acetate (3:1)

Sources & evidence

ORD record
ord-29ba291868e1405cbf62b1f703b29342
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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