Triethylamine → HCID 86755076, 화합물

HRID 850027

반응식

HRID 850027 반응식
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11]([C:13]1[CH:26]=[CH:25][C:16]([CH2:17][N:18]2[C:22]([CH:23]=O)=[CH:21][N:20]=[CH:19]2)=[CH:15][CH:14]=1)#[N:12].C(N(CC)CC)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(C(Cl)Cl)(Cl)Cl.CCOC(C)=O>[C:11]([C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[C:22]([CH2:23][CH:9]3[CH2:10][C:5]4[CH:4]=[CH:3][S:2][C:6]=4[NH:7][CH2:8]3)=[CH:21][N:20]=[CH:19]2)=[CH:25][CH:26]=1)#[N:12]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chlorideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

생성물 1

HCID 86755076HCID 86755076, 화합물

시약·촉매·용매 2

HCID 65911,1,2,2-Tetrachloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine hydrochloride (Halczenko and Hartman; Synthetic Commun., 1996, 26, 1363; 0.439 g, 2.5 mmol) in CHCl2CHCl2 (15 mL) was added 1-(4-cyanobenzyl)-5-imidazole carboxaldehyde (0.58 g, 2.75 mmol), 4 Å sieves and triethylamine (0.35 mL, 2.5 mmol) followed by NaBH(OAc)3 (1.59 g, 7.5 mmol). The mixture was stirred at room temperature for 16 h., the mixture was diluted with EtOAc, filtered through celite, washed with brine, dried (Na2SO4) and concentrated. The residue was stirred in 2N HCl (50 mL) for 2 h. then extracted with ether. The aqueous layer was basified with 40% NaOH solution and extracted 3× CH2Cl2 which was then washed with brine, dried (Na2SO4) and the solvent evaporated in vacuo. Chromatography (silica gel; 2.5% MeOH in CHCl3) followed by crystallization from ether afforded the title compound as a white solid.

후처리

  1. filtrationfiltered through celite
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. stirringThe residue was stirred in 2N HCl (50 mL) for 2 h.
  6. extractionthen extracted with ether
  7. extractionextracted 3× CH2Cl2 which
  8. washwas then washed with brine
  9. dry with materialdried (Na2SO4)
  10. customthe solvent evaporated in vacuo
  11. customChromatography (silica gel; 2.5% MeOH in CHCl3) followed by crystallization from ether

출처 및 근거

ORD 기록
ord-3396347695614d22be0f30b5f8dc4b87
출처 데이터셋
uspto-grants-2000_01
특허 번호
US06015817

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