1,2-Dichloroethane → 6-Hydroxynicotinamide

HRID 899699ノート

反応式

HRID 899699 の反応式
[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

参加物

8

反応物 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、化合物

生成物 1

HCID 729256-Hydroxynicotinamide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-f82d639c2f3a420d8047a5833b4bcca3
出典データセット
uspto-grants-2008_04
特許番号
US07354932B2

反応ノート

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