Dimethylformamide → HCID 25205987, compound

HRID 2068003Notes

Reaction equation

HRID 2068003 reaction equation
CN(C=O)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:10][NH:11][C:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20]I)[N:19]=1)=[O:13].[CH3:26][C:27]1[C:31]([S:32]([O-:34])=[O:33])=[C:30]([CH3:35])[O:29][N:28]=1.[Na+]>O>[Cl:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[Cl:25])[CH2:10][NH:11][C:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][S:32]([C:31]2[C:27]([CH3:26])=[N:28][O:29][C:30]=2[CH3:35])(=[O:34])=[O:33])[N:19]=1)=[O:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 23697072HCID 23697072, compoundHCID 58055059HCID 58055059, compound2×

Product 1

HCID 25205987HCID 25205987, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF (0.30 mL) solution of Intermediate 6: 1-(3,4-dichlorobenzyl)-3-(4-(iodomethyl)thiazol-2-yl)urea (45 mg, 0.10 mmol) and sodium 3,5-dimethylisoxazole-4-sulfinate (56 mg, 0.2 mmol, ˜60% pure) was stirred for an hour. The mixture was diluted with water and extracted with EtOAc. The organics were washed with brine, dried and evaporated to a residue that was purified by chromatography (silica gel) to afford the title compound. 1H NMR (400 MHz, CDCl3): 9.80 (1H, br), 7.39 (m, 2H), 7.15 (dd, 1H), 6.77 (s, 1H), 4.42 (d, 2H), 4.37 (s, 2H), 2.37 (s, 3H), 2.22 (s, 3H). MS (ES+): M/Z 475 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. washThe organics were washed with brine
  3. customdried
  4. customevaporated to a residue that
  5. customwas purified by chromatography (silica gel)

Sources & evidence

ORD record
ord-ad09c709615740c3920d71123bc438e6
Source dataset
uspto-grants-2012_10
Patent number
US08293919B2

Reaction notes

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