Triethylamine → HCID 86755076、化合物

HRID 850027

反応式

HRID 850027 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 86755076HCID 86755076、化合物

試薬・触媒・溶媒 2

HCID 65911,1,2,2-Tetrachloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3396347695614d22be0f30b5f8dc4b87
出典データセット
uspto-grants-2000_01
特許番号
US06015817

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