1,1-Dichloroethane → HCID 178473725、化合物

HRID 849424ノート

反応式

HRID 849424 の反応式
Cl.Cl.Cl.[NH:4]1[CH:8]=[C:7]([CH2:9][N:10]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]4[CH:22]=N[CH:24]=[CH:25][CH:26]=4)=[CH:20][C:15]=3[CH2:14][N:13]([C:27](=[O:32])[C:28](F)(F)F)[CH:12]([CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:11]2)[N:6]=[CH:5]1.[CH:40](C1N=CNC=1)=O.[Cl:47]C(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.[OH-].[NH4+].C(O)(=O)C>[ClH:47].[C:27]([N:13]1[CH2:14][C:15]2[CH:20]=[C:19]([C:21]3[CH:22]=[CH:40][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:17][C:16]=2[N:10]([CH2:9][C:7]2[N:6]=[CH:5][NH:4][CH:8]=2)[CH2:11][C@H:12]1[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)(=[O:32])[CH3:28]

参加物

8

反応物 4

HCID 63651,1-DichloroethaneHCID 764281H-Imidazole-4-carbaldehyde2 回HCID 5049666Sodium triacetoxyborohydride2 回HCID 178478619HCID 178478619、化合物

生成物 1

HCID 178473725HCID 178473725、化合物収率 48%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒HCID 14923Ammonium Hydroxide溶媒

反応条件

温度
60 °C

実験手順

A solution of Compound B (140 mg, 0.35 mmol), 4-formyl imidazole (68 mg, 0.7 mmol), dichloroethane (2 mL) and acetic acid (2 mL) was stirred at room temperature for 30 min and sodium triacetoxyborohydride (150 mg, 0.7 mmol) was added. The solution was heated to 60° C., stirred for 18 hour, and additional portions of 4-formyl imidazole and sodium triacetoxyborohydride were added (0.2 mmol each, 4 portions over 8 hours); the mixture was diluted with ethyl acetate (20 mL) and ammonium hydroxide (5 ml, conc), and stirred for an additional 30 min. The mixture was extracted with ethyl acetate (2×25 mL) and the combined organic extracts were washed with aqueous sodium bicarbonate (25 ml, saturated solution), and then ammonium chloride (25 mL, sat aqueous solution), dried (Na2SO4), and concentrated in vacuo to a semi-solid. The crude was purified by preparative HPLC (aqueous methanol gradient containing 0.1% TFA, C-18 column) and lyophilized to provide Compound C as a white solid (80 mg, 48%). MS: (M+H)+ 471

後処理

  1. stirringstirred for an additional 30 min
  2. extractionThe mixture was extracted with ethyl acetate (2×25 mL)
  3. washthe combined organic extracts were washed with aqueous sodium bicarbonate (25 ml, saturated solution)
  4. dry with materialammonium chloride (25 mL, sat aqueous solution), dried (Na2SO4)
  5. concentrationconcentrated in vacuo to a semi-solid
  6. customThe crude was purified by preparative HPLC (aqueous methanol gradient containing 0.1% TFA, C-18 column)

出典と根拠

ORDレコード
ord-43be0825aa844e8db0ad28ca6da308b4
出典データセット
uspto-grants-2000_01
特許番号
US06011029

反応ノート

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