1,2-Dichloroethane → 6-Hydroxynicotinamide

HRID 899699노트

반응식

HRID 899699 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][N:3]=1.C(Cl)CCl.C1C=CC2N(O)N=[N:21]C=2C=1.N1C2C=CC=CC=2N=C1CN(C1C2N=CC=CC=2CCC1)CCCCN>CN(C=O)C.O.C(OCC)(=O)C>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:21])=[O:7])=[CH:4][N:3]=1

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 10126019N'-(1H-benzimidazol-2-ylmethyl)-N'-(5,6,7,8-tetrahydroquinolin-8-yl)butane-1,4-diamineHCID 178418479HCID 178418479, 화합물

생성물 1

HCID 729256-Hydroxynicotinamide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 6-hydroxynicotinic acid (0.049 g, 0.35 mmoles) in DMF (2.7 mL) was added EDC (0.083 g, 0.43 mmoles), HOBT (0.056 g, 0.41 mmoles) and N1-(1H-Benzimidazol-2-ylmethyl)-N1-(5,6,7,8-tetrahydro-quinolin-8-yl)-butane-1,4-di amine (0.1 g, 0.29 mmoles) and the reaction stirred overnight at room temperature. Ethyl acetate (40 mL) and water (25 mL) were added and the organic layer was washed with brine (30 mL) and saturated aqueous NaHCO3 (30 mL). The aqueous layers were extracted with ethyl acetate (3×30 mL) and the combined organic extracts dried with Na2SO4 and concentrated. The crude product was purified by radial chromatography on silica gel (1 mm plate, 2% MeOH/1% NH4OH/CH2Cl2, then 10% MeOH/1% NH4OH/CH2Cl2) to give N-{4-[1H-benzolimidazol-2-ylmethyl)-(5,6,7,8-tetrahydroquinolin-8-yl)-amino]-butyl}-6-hydroxynicotinamide as an offwhite foam (30 mg, 16%).

후처리

  1. washthe organic layer was washed with brine (30 mL) and saturated aqueous NaHCO3 (30 mL)
  2. extractionThe aqueous layers were extracted with ethyl acetate (3×30 mL)
  3. dry with materialthe combined organic extracts dried with Na2SO4
  4. concentrationconcentrated
  5. customThe crude product was purified by radial chromatography on silica gel (1 mm plate, 2% MeOH/1% NH4OH/CH2Cl2

출처 및 근거

ORD 기록
ord-f82d639c2f3a420d8047a5833b4bcca3
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07354932B2

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