Water → HCID 178451899, compound

HRID 923385Notes

Reaction equation

HRID 923385 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]1[CH:46]=[CH:45][C:29]2[NH:30][C:31]([C@@H:33]3[CH2:37][CH2:36][CH2:35][N:34]3[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[N:32][C:28]=2[CH:27]=1.O>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]([CH2:25][C:26]2[CH:46]=[CH:45][C:29]3[NH:30][C:31]([C@@H:33]4[CH2:37][CH2:36][CH2:35][N:34]4[C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])=[N:32][C:28]=3[CH:27]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:16][CH:17]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 96956Benzenemethanamine, 4-nitro-N-phenyl-HCID 178451895HCID 178451895, compound

Product 1

HCID 178451899HCID 178451899, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 20A (0.530 g, 2.32 mmol) and K2CO3 (0.802 g, 5.81 mmol) were combined in dry DMF (20 mL) at room temperature, and nitrogen was bubbled through the solution for 10 min. The product from Example 7C (1.0 g, 2.63 mmol) was added in three equal portions in 20 min. intervals, and the reaction was stirred a total of 2.5 h. The mixture was poured into water, extracted into EtOAc, washed with brine. The organic was dried (MgSO4), filtered and evaporated. The product was purified by chromatography on silica gel, eluting with c 0-4% MeOH in CH2Cl2, and a second column eluting with 0-5% EtOAc in CH2Cl2 to give the title compound (0.350 g, 28.6% yield).

Workup

  1. customnitrogen was bubbled through the solution for 10 min
  2. extractionextracted into EtOAc
  3. washwashed with brine
  4. dry with materialThe organic was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe product was purified by chromatography on silica gel
  8. washeluting with c 0-4% MeOH in CH2Cl2
  9. washa second column eluting with 0-5% EtOAc in CH2Cl2

Sources & evidence

ORD record
ord-e88897c43b744a848e772e55f9999a2d
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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