Dimethylformamide → HCID 12074648, compound

HRID 2414359Notes

Reaction equation

HRID 2414359 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[O:13].[B-](F)(F)(F)F.[CH3:29][CH2:30][O:31]C(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C([N:49]([CH:52]([CH3:54])[CH3:53])CC)(C)C.[CH3:55][N:56]([CH3:59])[CH:57]=[O:58]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:49][CH:52]2[CH2:53][CH2:59][N:56]([C:57]([O:31][CH2:30][CH3:29])=[O:58])[CH2:55][CH2:54]2)=[O:8])=[CH:4][C:3]=1[NH:11][C:12]([NH:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])=[O:13]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 22645713HCID 22645713, compound

Product 1

HCID 12074648HCID 12074648, compound

Procedure

100 mg (0.28 mmol) of 4-chloro-3-[3-(2-chlorobenzoyl)ureido]benzoic acid, 93 mg (0.28 mmol) of TOTU and 37 mg (0.28 mmol) of diisopropylethylamine were coupled in 1 ml of dimethylformamide. The reaction solution was washed once each with 5% strength sodium bicarbonate solution and 10% strength citric acid solution, and the organic phase was dried and concentrated.

Workup

  1. washThe reaction solution was washed once each with 5% strength sodium bicarbonate solution and 10% strength citric acid solution
  2. customthe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d15ad64f7924dc19e6721290649e754
Source dataset
uspto-grants-2004_11
Patent number
US06812250B2

Reaction notes

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