DL-2-Phenoxypropionic acid → HCID 69421888, compound

HRID 1349710Notes

Reaction equation

HRID 1349710 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14](C#N)[CH:15]=3)[N:10]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[O:25]([CH:32]([CH3:36])[C:33]([OH:35])=O)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.[CH3:38][N:39](C)CCCN=C=NCC>ClCCl>[C:38]([CH:22]1[CH2:21][O:20][CH:19]([N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:33](=[O:35])[CH:32]([O:25][C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH3:36])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)[CH2:24][CH2:23]1)#[N:39]

Participants

5

Reactant 3

HCID 13658DL-2-Phenoxypropionic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480146HCID 22480146, compound

Product 1

HCID 69421888HCID 69421888, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.300 g, 0.94 mmol) in dichloromethane (10 mL) was added 2-phenoxy propionic acid (0.172 g, 1.034 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.216 g, 1.13 mmol). After overnight reaction at room temperature, the reaction mixture was partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and evaporated to dryness. The title compound was purified by column chromatography (SiO2, 25% ethyl acetate in hexanes) (0.370 g, 84%): ES-MS (m/z) 489 [M+Na], 467 [M+H]+.

Workup

  1. customAfter overnight reaction at room temperature
  2. customthe reaction mixture was partitioned between dichloromethane and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated to dryness
  5. customThe title compound was purified by column chromatography (SiO2, 25% ethyl acetate in hexanes) (0.370 g, 84%)

Sources & evidence

ORD record
ord-6388ec19a6c44c20a6eba4dec757afa4
Source dataset
uspto-grants-2007_05
Patent number
US07211594B2

Reaction notes

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