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

HRID 1766201ノート

反応式

HRID 1766201 の反応式
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]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 24408Bromine2 回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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

  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)

出典と根拠

ORDレコード
ord-fc2f03d7458941e794d75feba2b67619
出典データセット
uspto-grants-2007_06
特許番号
US07230001B1

反応ノート

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