Potassium Carbonate → HCID 70163829, compound

HRID 1250233Notes

Reaction equation

HRID 1250233 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[C:21]([O:28][CH3:29])[CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]2[CH2:30]Br)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[SH:32][C:33]1[S:34][C:35]([CH3:38])=[N:36][N:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][N:17]2[C:26](=[O:27])[C:25]3[C:20](=[C:21]([O:28][CH3:29])[CH:22]=[CH:23][CH:24]=3)[N:19]=[C:18]2[CH2:30][S:32][C:33]2[S:34][C:35]([CH3:38])=[N:36][N:37]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 70165804HCID 70165804, compoundHCID 178434161HCID 178434161, compound

Product 1

HCID 70163829HCID 70163829, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the product from Step A (137 mg, 0.28 mmol), 2-mercapto-5-methyl-1,3,4-thiadiazole (37 mg, 0.28 mmol), and potassium carbonate (77 mg, 0.56 mmol) in DMF (15 mL) was stirred at 50° C. for 17 h. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic solution was washed with sat'd aq NaHCO3, sat'd aq NaCl, dried and concentrated. The crude residue was purified using SiO2-gel chromatography using 50% EtOAc/hexanes to yield the desired product as a yellow solid. API-MS: 546 (M+1). 1H NMR (300 MHz, CDCl3): d 7.8 (d, 1 H), 7.4 (t, 1 H), 7.2 (d, 1 H), 4.95 (s, 2 H), 4.1 (t, 2 H), 4.0 (s, 3 H), 2.75 (s, 3 H), 2.8 (t, 3 H), 1.8-1.0 (m), 1.45 (s, 9 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe organic solution was washed with sat'd aq NaHCO3
  3. customdried
  4. concentrationconcentrated
  5. customThe crude residue was purified

Sources & evidence

ORD record
ord-36f7be6f41c04da8afb7758b17938b2e
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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