Dabco → HCID 59146117, compound

HRID 1512767Notes

Reaction equation

HRID 1512767 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[NH:24][CH:23]=[C:22]4[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[C:34](=O)(OC)OC.C1N2CCN(CC2)C1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:34])[CH:23]=[C:22]4[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 9237DabcoHCID 12021Dimethyl CarbonateHCID 59146155HCID 59146155, compound

Product 1

HCID 59146117HCID 59146117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-3-yl]butanoate (D53) (150 mg) and dimethyl carbonate (5.0 mL) in N,N-dimethylformamide (DMF) (0.5 mL) was added DABCO (18 mg). The reaction vessel was sealed and heated in Biotage Initiator using initial normal to 150° C. for 1.5 h. After cooling the reaction, the mixture was concentrated to afford the crude product ethyl 4-[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]butanoate (D57) (180 mg), which was used for the next hydrolysis step without further purification. MS (ES): C26H28ClN3O4 requires 481. found 482.2 (M+H+).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated in Biotage Initiator
  3. customnormal to 150° C.
  4. customfor 1.5 h
  5. temperatureAfter cooling
  6. customthe reaction
  7. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-0af9cbc0650740be9fba70a4b26135fe
Source dataset
uspto-grants-2012_07
Patent number
US08217028B2

Reaction notes

Loading…