Citric Acid → 1-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone

HRID 1766196Notes

Reaction equation

HRID 1766196 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([OH:14])=O)=[CH:4][C:3]=1[Br:16].[NH:17]1[CH2:22][CH2:21][CH:20]([N:23]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[NH:25][C:24]2=[O:34])[CH2:19][CH2:18]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[K+].[Br-].BrBr>O.O1CCCC1>[NH2:1][C:2]1[C:3]([Br:16])=[CH:4][C:5]([C:9](=[O:15])[CH2:10][CH2:11][C:12]([N:17]2[CH2:18][CH2:19][CH:20]([N:23]3[CH:27]=[C:26]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[NH:25][C:24]3=[O:34])[CH2:21][CH2:22]2)=[O:14])=[CH:6][C:7]=1[Br:8]

Participants

10

Reactant 7

HCID 311Citric AcidHCID 24408BromineHCID 81531DiisopropylethylamineHCID 253877Potassium BromideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 11175554HCID 11175554, compoundHCID 113455464-Phenyl-1-(piperidin-4-yl)-1,3-dihydro-2H-imidazol-2-one

Product 1

HCID 98944161-{1-[4-(4-amino-3,5-dibromophenyl)-1,4-dioxobutyl]-4-piperidinyl}-1,3-dihydro-4-phenyl-2(2H)-imidazolone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.0 g (2.849 mmol) of 4-amino-3,5-dibromo-γ-oxo-benzenebutanoic acid, 1.04 g (2.91 mmol) of 1,3-dihydro-1-(4-piperidinyl)-4-phenyl-2(2H)-imidazolone, 0.935 g (2.912 mmol) of TBTU, 1.02 ml (5.77 mmol) of DIEA and 50 ml of tetrahydrofuran was stirred for 1 hour at ambient temperature. The reaction mixture was diluted with 300 ml of water and acidified slightly with citric acid. The precipitate formed was suction filtered and washed carefully with water, then with 3 ml of tetrahydrofuran, and finally dried in a circulating air dryer at a temperature of 60° C. 1.3 g (79% of theoretical) of a colourless, crystalline product were obtained, Rf 0.47 (El A). IR (KBr): 1679.9 cm−1 (C═O) MS: M+=574/576/578 (Br2)

Workup

  1. customThe precipitate formed
  2. filtrationfiltered
  3. washwashed carefully with water
  4. dry with materialwith 3 ml of tetrahydrofuran, and finally dried in a circulating air dryer at a temperature of 60° C
  5. custom1.3 g (79% of theoretical) of a colourless, crystalline product were obtained

Sources & evidence

ORD record
ord-d58ad67c24ac41cbb83f7bce5ef521dd
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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