Triethylamine → HCID 57659431, compound

HRID 217198Notes

Reaction equation

HRID 217198 reaction equation
[CH2:1]([O:5][C:6](Cl)=[O:7])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.[NH:16]1[CH2:21][CH2:20][CH:19]([CH2:22][C:23]2[N:27]=[C:26]([C:28]3[O:36][C:35]4[CH:34]=[CH:33][N:32]=[C:31]([C:37]#[N:38])[C:30]=4[CH:29]=3)[O:25][N:24]=2)[CH2:18][CH2:17]1>C(Cl)Cl.CCOCC.O>[CH2:1]([O:5][C:6]([N:16]1[CH2:17][CH2:18][CH:19]([CH2:22][C:23]2[N:27]=[C:26]([C:28]3[O:36][C:35]4[CH:34]=[CH:33][N:32]=[C:31]([C:37]#[N:38])[C:30]=4[CH:29]=3)[O:25][N:24]=2)[CH2:20][CH2:21]1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11652480HCID 11652480, compound

Product 1

HCID 57659431HCID 57659431, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

i-BuOCOCl (19 μL, 146 μmol) and NEt3 (15 μL, 107 μmol) were added to a stirred solution of 2-(3-piperidin-4-ylmethyl-[1,2,4]oxadiazol-5-yl)furo[3,2-c]pyridine-4-carbonitrile (Preparation 15, 30 mg, 97 μmol) in anhydrous CH2Cl2 (1.5 mL). After 30 min, the reaction mixture was diluted with Et2O (10 mL) and H2O (2 mL). The organic layer was washed with saturated aqueous Na2CO3 (2 mL), H2O (2 mL), and brine (2 mL), before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (EtOAc) furnished the title compound: RT=3.95 min; m/z (ES+)=410.1 [M+H]+.

Workup

  1. washThe organic layer was washed with saturated aqueous Na2CO3 (2 mL), H2O (2 mL), and brine (2 mL)
  2. dry with materialbefore being dried (MgSO4)
  3. filtrationFiltration, solvent evaporation, and column chromatography (EtOAc)

Sources & evidence

ORD record
ord-8ee6d721192e4040863e5454d1e01c95
Source dataset
uspto-grants-2012_06
Patent number
US08193359B2

Reaction notes

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