1,1-Dichloroethane → HCID 178473725, 화합물

HRID 849424노트

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HRID 849424 반응식
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]

참가 물질

8

반응물 4

HCID 63651,1-DichloroethaneHCID 764281H-Imidazole-4-carbaldehyde2회HCID 5049666Sodium triacetoxyborohydride2회HCID 178478619HCID 178478619, 화합물

생성물 1

HCID 178473725HCID 178473725, 화합물수율 48%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8857Ethyl Acetate용매HCID 14923Ammonium Hydroxide용매

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온도
60 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-43be0825aa844e8db0ad28ca6da308b4
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06011029

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