Potassium Carbonate → HCID 68752981, compound

HRID 390368Notes

Reaction equation

HRID 390368 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:32][C:10]3([CH2:15][CH2:14][N:13]([C:16]4[S:20][C:19]([C:21]5[N:22]=[N:23][N:24]([CH2:26][C:27]([O:29]CC)=[O:28])[N:25]=5)=[N:18][N:17]=4)[CH2:12][CH2:11]3)[CH:9]=2)=[CH:4][CH:3]=1.FC1C=CC(C2C3C(=CC=CC=3)OC3(CCNCC3)C=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>COCCOC.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:32][C:10]3([CH2:15][CH2:14][N:13]([C:16]4[S:20][C:19]([C:21]5[N:22]=[N:23][N:24]([CH2:26][C:27]([OH:29])=[O:28])[N:25]=5)=[N:18][N:17]=4)[CH2:12][CH2:11]3)[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66960235HCID 66960235, compoundHCID 68750584HCID 68750584, compound

Product 1

HCID 68752981HCID 68752981, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
81 °C

Procedure

Ethyl 2-(5-(5-(4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine]-1′-yl)-1,3,4-thiadiazol-2-yl)-2H-tetrazol-2-yl)acetate A mixture of 4-(4-fluorophenyl)spiro[chromene-2,4′-piperidine] (171 mg, 0.58 mmol) (Example 6, Step 2), Intermediate 2 (203 mg, 0.64 mmol) and K2CO3 (144 mg, 1.04 mmol) was suspended in dry DME (3 mL). The reaction mixture was stirred under N2 at an external temperature of 81° C. for 1.5 h. Then the reaction mixture was cooled down to room temperature, diluted with DCM (5 mL), washed with 5% KHSO4 (10 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The resulting oily residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 10-60% EtOAc/hexanes) to afford the title compound as an oil.

Workup

  1. temperatureThen the reaction mixture was cooled down to room temperature
  2. washwashed with 5% KHSO4 (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting oily residue was purified by Combiflash™ chromatography (SiO2 (12 g), eluting with 10-60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a4253ba5478a4e5fb773b703a463e293
Source dataset
uspto-grants-2013_02
Patent number
US08383643B2

Reaction notes

Loading…