Hydrochloric Acid → 5-aminocarbonylamino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone

HRID 1766201Notes

Reaction equation

HRID 1766201 reaction equation
Cl.[O-:2][C:3]#[N:4].[Na+].[NH2:6][C:7]1[CH:36]=[CH:35][C:10]2[N:11]([CH:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][C:24]([C:26]4[CH:31]=[C:30]([Br:32])[C:29]([NH2:33])=[C:28]([Br:34])[CH:27]=4)=[O:25])[CH2:17][CH2:16]3)[C:12](=[O:14])[NH:13][C:9]=2[CH:8]=1.[K+].[Br-].BrBr>C1COCC1>[NH2:4][C:3]([NH:6][C:7]1[CH:36]=[CH:35][C:10]2[N:11]([CH:15]3[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][C:24]([C:26]4[CH:31]=[C:30]([Br:32])[C:29]([NH2:33])=[C:28]([Br:34])[CH:27]=4)=[O:25])[CH2:19][CH2:20]3)[C:12](=[O:14])[NH:13][C:9]=2[CH:8]=1)=[O:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 24408Bromine2×HCID 253877Potassium BromideHCID 517096Sodium CyanateHCID 211098785-amino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone

Product 1

HCID 211098795-aminocarbonylamino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.5 ml of 1N hydrochloric acid, followed by 47 mg (0.723 mmol) of sodium cyanate were added to a solution of 200 mg (0.363 mmol) of 5-amino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone in 5 ml of THF at a reaction temperature of 0° C. The ice bath was removed and the mixture was stirred overnight at ambient temperature. The orange-coloured solution was carefully combined with 100 ml of conc. aqueous sodium hydrogen carbonate solution and overlaid with 50 ml of tert.butylmethyl ether. The precipitate formed was suction filtered and purified by column chromatography on silica gel (30–60 μm) using dichloromethane/methanol/cyclohexane/conc. ammonia 400/40/40/2.5 v/v/v/v as eluant. By working up the appropriate fractions 106 mg (44% of theoretical) of the desired compound were obtained in the form of colourless crystals (THF/diethylether 1/1 v/v)), Rf 0.12 (El B). IR (KBr): 3435.0, 3354.0 (NH, NH2); 1701.1, 1662.5 (C═O) MS: ESI: (M+H)+=593/595/597 (Br2); (M+Na)+615/617/619 (Br2)

Workup

  1. customThe ice bath was removed
  2. customThe precipitate formed
  3. filtrationfiltered
  4. custompurified by column chromatography on silica gel (30–60 μm)
  5. customwere obtained in the form of colourless crystals (THF/diethylether 1/1 v/v)), Rf 0.12 (El B)

Sources & evidence

ORD record
ord-fc2f03d7458941e794d75feba2b67619
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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