Water → HCID 66826552, compound

HRID 2037197Notes

Reaction equation

HRID 2037197 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[O:10][N:9]=[C:8]([C:11]3([C:15]4[CH:16]=[CH:17][C:18]([C:21]5N=[CH:23][C:24]([NH2:27])=[N:25][CH:26]=5)=[N:19][CH:20]=4)[CH2:14][CH2:13][CH2:12]3)[N:7]=2)[CH:3]=[N:2]1.[C:28](=O)([O-])[O-].[K+].[K+].O.C[CH2:36][O:37][C:38]([CH3:40])=O>CN(C=O)C>[O:37]1[CH2:36][CH:40]([N:1]2[CH:5]=[C:4]([C:6]3[O:10][N:9]=[C:8]([C:11]4([C:15]5[CH:16]=[CH:17][C:18]([C:21]6[CH:26]=[N:25][C:24]([NH2:27])=[CH:23][CH:28]=6)=[N:19][CH:20]=5)[CH2:12][CH2:13][CH2:14]4)[N:7]=3)[CH:3]=[N:2]2)[CH2:38]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 136352323HCID 136352323, compound

Product 1

HCID 66826552HCID 66826552, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of R67 (50 mg, 0.14 mmol), R38 (51 mg, 0.28 mmol) and potassium carbonate (38 mg, 0.28 mmol) in DMF (2 ml) are stirred at 80° C. over night. After this time the reaction is cooled to room temperature and poured into water and EtOAc. The layers are separated and the aqueous phase is extracted twice more with EtOAc. The combined organics are dried (MgSO4), filtered and concentrated. The remaining residue is purified via flash chromatography (Silica gel, 0-8% MeOH/DCM) to afford the title compound (35 mg); m/z 417.3 [M+H].

Workup

  1. temperatureAfter this time the reaction is cooled to room temperature
  2. customThe layers are separated
  3. extractionthe aqueous phase is extracted twice more with EtOAc
  4. dry with materialThe combined organics are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe remaining residue is purified via flash chromatography (Silica gel, 0-8% MeOH/DCM)

Sources & evidence

ORD record
ord-7afa60564abd4a99be2ccc8824dc5f23
Source dataset
uspto-grants-2013_11
Patent number
US08575201B2

Reaction notes

Loading…