1,2-Dichloroethane → Ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoate

HRID 2189736Notes

Reaction equation

HRID 2189736 reaction equation
[OH:1][NH:2][C:3](=[NH:20])[C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:7]2.[Cl:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[C:25](O)=O.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.CCOC(C)=O>[Cl:21][C:22]1[CH:23]=[C:24]([C:25]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][CH:12]=3)[N:9]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:8]=[CH:7]4)[N:20]=2)[CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:33])[CH3:34]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 225977283-Chloro-4-(propan-2-yloxy)benzoic acidHCID 178471847HCID 178471847, compound

Product 1

HCID 59316704Ethyl 3-[5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indazol-1-yl]propanoateYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A solution of Ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (2.04 g, 7.38 mmol), 3-chloro-4-[(1-methylethyl)oxy]benzoic acid (D3) (1.743 g, 8.12 mmol), EDC (2.123 g, 11.08 mmol) and HOBT (1.357 g, 8.86 mmol) in N,N-Dimethylformamide (DMF) (25 ml) was stirred overnight then heated at 120° C. during 4 hours. The mixture was dissolved in EtOAc then washed with water and NaHCO3 and purified by flash chromatography, eluting with EtOAc/iso-Hexane 10-90% then 10-30%. The solvent was evaporated to give (1.95 g) of white solid. MS (ES): C23H2335ClN4O4 requires 454; found (MH+) 455.

Workup

  1. washthen washed with water and NaHCO3
  2. custompurified by flash chromatography
  3. washeluting with EtOAc/iso-Hexane 10-90%
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-6215c2085b944bb28635e77e81a0c93a
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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