Triethylamine → HCID 131724911, compound

HRID 2183213Notes

Reaction equation

HRID 2183213 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]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](Cl)=[O:31].[CH2:33]([N:35](CC)CC)C>O1CCCC1>[C:33]([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:30]([C:26]4[O:25][CH:29]=[CH:28][CH:27]=4)=[O:31])[CH:7]=[CH:6][CH:5]=3)=[N:9]2)[CH2:24][CH2:23]1)#[N:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 22480146HCID 22480146, compound

Product 1

HCID 131724911HCID 131724911, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 tetrahydrofuran (10 mL), was added 2-furoyl chloride (0.139 mL, 1.41 mmol) and triethyl amine (0.655 mL, 4.7 mmol). After stirring at room temperature overnight, the reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic phase was dried under vacuum and the title product was purified by column chromatography (SiO2, 20-30% ethyl acetate in hexanes) (0.370 g, 95%): ES-MS (m/z) 413 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customThe organic phase was dried under vacuum
  4. customthe title product was purified by column chromatography (SiO2, 20-30% ethyl acetate in hexanes) (0.370 g, 95%)

Sources & evidence

ORD record
ord-0f198214d234418ebd5cfe19156b07d7
Source dataset
uspto-grants-2005_05
Patent number
US06897231B2

Reaction notes

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