Water → HCID 58474503, compound

HRID 1400842Notes

Reaction equation

HRID 1400842 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:17][C:16]3[C:11](=[N:12][CH:13]=[CH:14][C:15]=3[O:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][C:20]=3[F:28])[CH:10]=2)=[N:7][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].[C:35]1(=[O:41])[NH:39][C:38](=[O:40])[CH2:37][CH2:36]1.O>CN(C=O)C>[F:28][C:20]1[CH:21]=[C:22]([N+:25]([O-:27])=[O:26])[CH:23]=[CH:24][C:19]=1[O:18][C:15]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:10]=[C:9]([C:6]3[N:7]=[CH:8][C:3]([CH2:2][N:39]4[C:35](=[O:41])[CH2:36][CH2:37][C:38]4=[O:40])=[CH:4][CH:5]=3)[S:17][C:16]=12

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11439SuccinimideHCID 58474527HCID 58474527, compound

Product 1

HCID 58474503HCID 58474503, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 102 (200 mg, 0.481 mmol, scheme 26) in DMF (5 mL) was added Cs2CO3 (313 mg, 0.962 mmol) and succinimide (95 mg, 0.962 mmol) and the reaction mixture was stirred at RT for 4 hours. The reaction mixture was poured into water and extracted with EtOAc. The organic phase was collected, dried over anhydrous Na2SO4, filtered and concentrated to afford title compound 138 (100 mg, 43% yield) that was triturated with Et2O and used with no additional purification. MS (m/z)=479.50 (M+H)

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phase was collected
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-624d751a40ca49918911cb6329a53973
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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