Potassium Carbonate → HCID 86729965, compound

HRID 2205278Notes

Reaction equation

HRID 2205278 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:31])[S:9]([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24]C)=[O:23])=[CH:20][N:19]=2)=[O:16])(=[O:11])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CCO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH3:31])[S:9]([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[C:15]([NH:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([OH:24])=[O:23])=[CH:20][N:19]=2)=[O:16])(=[O:10])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86729966HCID 86729966, compound

Product 1

HCID 86729965HCID 86729965, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

Compound 65-b was prepared by stirring 65 (20 mg, 0.043 mmol) in EtOH/H2O (1:1, 4 mL) and K2CO3 (11.9 mg, 0.086 mmol) overnight at room temperature. Reaction mixture was then neutralized to PH 3.0, extracted with EtOAc and then dried over MgSO3 to generate 17 mg of 65-b (90%). 1H NMR (500 MHz, CDCl3) δ 3.20 (s, 3H), 7.05 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 7.64 (t, J=7.8 Hz, 1H), 7.70 (d, J=7.9 Hz, 1H), 8.13 (s, 1H), 8.18 (d, J=7.7 Hz, 1H), 8.38 (dd, J=2.2, 8.8 Hz, 1H), 8.43 (d, J=8.7 Hz, 1H), 8.84 (s, 1H), 8.91 (d, J=1.6 Hz, 1H). 13C NMR (126 MHz, CDCl3) δ 38.27, 52.35, 113.18, 122.67, 126.22, 127.84, 129.34, 129.78, 131.40, 131.81, 133.62, 134.77, 137.37, 139.49, 140.02, 150.09, 153.94, 163.93, 165.23. LCQ (M−H+) calcd C20H16ClN3O5S 444. found 444.

Workup

  1. customReaction mixture
  2. extractionextracted with EtOAc
  3. dry with materialdried over MgSO3

Sources & evidence

ORD record
ord-e8797f4167184dc19a373d957555d677
Source dataset
uspto-grants-2016_06
Patent number
US09371277B2

Reaction notes

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