Potassium Carbonate → HCID 22508909, compound

HRID 1163055Notes

Reaction equation

HRID 1163055 reaction equation
[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:23]4[CH2:25][O:24]4)=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[NH:6]2.[CH3:28][N:29]([CH3:34])[S:30]([NH2:33])(=[O:32])=[O:31].[C:35](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[F:1][C:2]1[C:10]([O:11][C:12]2[C:17]3=[C:18]([CH3:26])[C:19]([O:21][CH2:22][CH:23]([OH:24])[CH2:25][CH2:35][NH:33][S:30]([N:29]([CH3:34])[CH3:28])(=[O:32])=[O:31])=[CH:20][N:16]3[N:15]=[CH:14][N:13]=2)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:27])[NH:6]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 134472N,N-DimethylsulfamideHCID 22508879HCID 22508879, compound

Product 1

HCID 22508909HCID 22508909, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 2 (40 mg, 0.11 mmol), N,N-dimethylsulfamide (94 mg, 0.66 mmol) and potassium carbonate (91 mg, 0.66 mmol) in DMF (0.5 ml) was stirred at 80° C. for 1.5 h. The mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC, followed by chromatography on silica gel eluting with 10% methanol in ethyl acetate to afford the title compound (13.7 mg, 25% yield) as a white solid. MS: (M+H)+=493.1

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified by preparative HPLC

Sources & evidence

ORD record
ord-f0be806b552548c2a1945fc6406bfa88
Source dataset
uspto-grants-2010_10
Patent number
US07820814B2

Reaction notes

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