Acetic Acid → 1-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine

HRID 276774

反応式

HRID 276774 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[N:24]=[C:25]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)=[N:32][CH:33]=3)[NH:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22].C(O)(=O)C.[CH:44](=O)[CH:45]([CH3:47])[CH3:46]>C1COCC1.[OH-].[Na+].C(OCC)(=O)C>[Cl:15][C:16]1[CH:17]=[C:18]([C:23]2[NH:24][C:25]([C:28]3[CH:29]=[CH:30][C:31]([N:34]4[CH2:39][CH2:38][N:37]([CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:36][CH2:35]4)=[N:32][CH:33]=3)=[N:26][CH:27]=2)[CH:19]=[CH:20][C:21]=1[Cl:22]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178477952{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine

生成物 1

HCID 98673341-{5-[5-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

Sodium triacetoxyborohydride (20.2 g) was added to a suspension of 1-{5-[4-(3,4-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-piperazine (23.8 g), acetic acid (5.1 mL), and isobutyraldehyde (6.35 mL) in THF (250 mL). The resultant suspension was stirred at ambient temperature for 18 hours, and then the reaction mixture was diluted with 1 N NaOH (1000 mL) and ethyl acetate (450 mL). The layers were separated, and the organic phase was diluted with hexanes (1000 mL). The resultant precipitate was collected by filtration, and the mother liquors were concentrated to 400 mL. The second crop of precipitate was collected and combined with the first crop to provide 1-{5-[5(3,4,-dichloro-phenyl)-1H-imidazol-2-yl]-pyridin-2-yl}-4-isobutyl-piperazine (22.5 g).

後処理

  1. customThe layers were separated
  2. additionthe organic phase was diluted with hexanes (1000 mL)
  3. filtrationThe resultant precipitate was collected by filtration
  4. concentrationthe mother liquors were concentrated to 400 mL
  5. customThe second crop of precipitate was collected

出典と根拠

ORDレコード
ord-f668ec788e3840d7b5efe71c30b22f9b
出典データセット
uspto-grants-2002_03
特許番号
US06355635B1

関連ノート

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