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

HRID 1766196ノート

反応式

HRID 1766196 の反応式
[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]

参加物

10

反応物 7

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-d58ad67c24ac41cbb83f7bce5ef521dd
出典データセット
uspto-grants-2007_06
特許番号
US07230001B1

反応ノート

読み込み中…