Aniline → HCID 23634300, compound

HRID 1158760Notes

Reaction equation

HRID 1158760 reaction equation
[C:1]1([N:7]2C(C([O-])=O)=CN=C2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C(OC(=O)CBr)(=O)C.Br[CH2:31][C:32]([NH:34][C:35]1[N:36]=[C:37]([N:53]([CH3:55])[CH3:54])[N:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]=1[C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[O:33].NC1C=CC=CC=1>C(Cl)Cl.CN(C=O)C>[CH3:54][N:53]([CH3:55])[C:37]1[N:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])=[C:35]([NH:34][C:32](=[O:33])[CH2:31][NH:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:36]=1

Participants

8

Reactant 5

HCID 6115AnilineHCID 8471TriethylamineHCID 7063771HCID 7063771, compoundHCID 53903227HCID 53903227, compoundHCID 57737449HCID 57737449, compound

Product 1

HCID 23634300HCID 23634300, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The 1-phenyl-1H-imidazole-5-carboxylate (1 equivalent (eq), 0.33 mmol) and triethylamine (2 eq, 0.66 mmol) were dissolved in DCM (5 mL) and bromoacetyl acetate (1.5 eq, 0.49 mmol) was added dropwise. The solution was stirred for 3 hours at room temperature. Then, the reaction was quenched with K2CO3 (aqueous (aq)) (1 M, 25 mL) and extracted with iPr2O. The organic layers were pooled, dried over Mg2SO4, filtered and evaporated. The residue was used directly without any further purification in the next step. The tert-butyl 4-[(bromoacetyl)amino]-2-(dimethylamino)-1-phenyl-1H-imidazole-5-carboxylate (1 eq) and aniline (2.5 eq) were dissolved in DMF (5 mL) and heated to 100° C. for 1 hour. The solution was evaporated and K2CO3(aq) (1 M, 25 mL) was added. The reaction mixture was subsequently extracted several times with i-Pr2O. The organic phases were pooled, dried over MgSO4, filtered and evaporated. Eventually the residue was purified by preparatory HPLC, which afforded the desired product.

Workup

  1. customThen, the reaction was quenched with K2CO3 (aqueous (aq)) (1 M, 25 mL)
  2. extractionextracted with iPr2O
  3. dry with materialdried over Mg2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was used directly without any further purification in the next step
  7. temperatureheated to 100° C. for 1 hour
  8. customThe solution was evaporated
  9. additionK2CO3(aq) (1 M, 25 mL) was added
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. customevaporated
  13. customEventually the residue was purified by preparatory HPLC, which

Sources & evidence

ORD record
ord-0f97f2382ac34847abafe6576df001ef
Source dataset
uspto-grants-2010_10
Patent number
US07812026B2

Reaction notes

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