1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Ethyl 3-(5-{5-[3-chloro-4-(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indazol-1-yl)propanoate

HRID 2189783Notes

Reaction equation

HRID 2189783 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][CH2:32][CH3:33])[C:25](O)=O.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[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][CH2:32][CH3:33]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 7209893-Chloro-4-ethoxybenzoic acidHCID 178471847HCID 178471847, compound

Product 1

HCID 59316698Ethyl 3-(5-{5-[3-chloro-4-(ethyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-1H-indazol-1-yl)propanoateYield 20.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-{5-[(hydroxyamino)(imino)methyl]-1H-indazol-1-yl}propanoate (D52) (265 mg, 0.96 mmol) and 3-Chloro-4-(ethyloxy)benzoic acid (D7) (192 mg, 0.96 mmol) were stirred together in DMF (5 ml) at 80° C. and EDAC (203 mg) and HOBt (142 mg) were added. When the reaction was judged to be complete (analysis by LCMS) it was cooled and the reaction mixture was partitioned between EtOAc and aq. sodium bicarbonate solution. The organic layer was separated and washed with water, dried and evaporated and triturated with ethanol to give the crude product. Purification by flash chromatography (EtOAc/hexane 1:3 to 1:1) to afforded the title compound (87 mg) as a white solid. MS (ES): C22H2135ClN4O4 requires 440 found (MH+) 441.

Workup

  1. temperaturewas cooled
  2. customthe reaction mixture was partitioned between EtOAc and aq. sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customtriturated with ethanol
  8. customto give the crude product
  9. customPurification by flash chromatography (EtOAc/hexane 1:3 to 1:1)

Sources & evidence

ORD record
ord-1e15310189534547a73f910fa1a3b681
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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