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

HRID 1766196노트

반응식

HRID 1766196 반응식
[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]

참가 물질

10

반응물 7

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-d58ad67c24ac41cbb83f7bce5ef521dd
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230001B1

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